Category: 31886-58-5

(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, cas is 31886-58-5, it is a common heterocyclic compound, the chiral-nitrogen-ligands compound, its synthesis route is as follows.

15.4 ml of a cyclohexane solution of s-butyllithium (1.3 M, 22 mmol) are added to a solution of 5.14 g (20 mmol) of (R)-N, N-dimethyl-1 -ferrocenylethylamine [(R)-ugi- amine] in 30 ml of t-butyl methyl ether (TBME) at <20C over a period of 10 minutes. The mixture is then heated to 00C while stirring and maintained at this temperature for 1.5 hours. It is then cooled to <60C and 3.0 ml (20 mmol) of dichlorocyclohexyl- phosphine are added over a period of 10 minutes. After stirring at -78C for30 minutes, the mixture is allowed to warm slowly to room temperature and is stirred at this temperature for 1.5 hours. With the rapid development of chemical substances, we look forward to future research findings about 31886-58-5 Reference£º
Patent; SOLVIAS AG; WO2008/55942; (2008); A1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.31886-58-5,(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine,as a common compound, the synthetic route is as follows.

6.0g (R) -1- ferrocenyl ethyldimethylamine was added 20mL of dry tert-butyl methyl ether, in an ice bath, under an argon atmosphere was slowly added dropwise 21.5mL 1.3mol / L tert-butyllithium n-hexane solution, warmed to room temperature after dropwise addition, reaction was stirred for 1 hour and then added dropwise dissolved in 20mL of MTBE to the reaction solution at -78 deg.] C 5.52g of p-toluenesulfonyl azide, after the reaction at -78 5 h, slowly warmed to 0 deg.] C, stirred for 10 minutes, dissolved in 250mL of distilled water was added 11.6g of sodium pyrophosphate decahydrate, stirred at room temperature overnight, the reaction was stopped extracted with dichloromethane (3 ¡Á 80mL), the organic layer was dried over anhydrous magnesium sulfate, and rotary evaporation to obtain a reddish black oil, separated by column chromatography (eluent volume of ethyl acetate and triethylamine as the 30: 1 mixture, silica gel 300 to 400 mesh), to give a red-brown oil azide 5.7g, yield of 82%.

The synthetic route of 31886-58-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Shaanxi Normal University; Chai Yonghai; Ren Xiaochen; He Chunyan; Chen Weiping; Zhang Shengyong; (14 pag.)CN104592313; (2017); B;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

31886-58-5, (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine is a chiral-nitrogen-ligands compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example B18: Reaction schemeX24 ml (10 mmol) of n-BuLi (2.5 M in hexane) are added dropwise to a solution of 3.44 g (10 mmol) of 1 ,1 ‘-dibromoferrocene in 10 ml of tetrahydrofuran (THF) at a temperature of < -30C. The mixture is stirred at this temperature for a further 1.5 hours. 2.21 ml (10 mmol) of dicyclohexylphosphine chloride are then added dropwise at such a rate that the temperature does not exceed -20C. After stirring the mixture for a further 10 minutes, the temperature is allowed to rise to room temperature and the mixture is stirred for another one hour. It is cooled back down to 30C and 4.4 ml (11 mmol) of n-BuLi (2.5 M in hexane) are added dropwise. The mixture is subsequently stirred at -10C for 30 minutes. The reaction mixture is then cooled to -78C and 1.49 ml (11 mmol) of dichlorophenylphosphine are added. The mixture is stirred at -78C for 20 minutes and then at room temperature for a further one hour. This gives a reaction mixture comprising the monochlorodiphosphine X6. In a second vessel, 8.5 ml (11 mmol) of S-BuLi (1.3 M in cyclohexane) are added dropwise to a solution of 2.57 g (10 mmol) of (R)-1-dimethylamino-1-ferrocenylethane in 15 ml of diethyl ether at <-10C. After stirring the mixture at the same temperature for 10 minutes, the temperature is allowed to rise to 0C and the mixture is stirred for another 1.5 hours. This reaction solution is subsequently added by means of a cannula to the reaction mixture comprising the monochlorodiphosphine X6 which has been cooled to -10C. After the addition, the mixture is stirred at room temperature for another 2 hours. After addition of 10 ml of water, the reaction mixture is extracted, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure on a rotary evaporator. The residue is heated at 140C for one hour. Column chromatography (silica gel 60; eluent: hexane/ethyl acetate 4:1 ) gives the compound of the formula (B1 ) in a yield of 47%. 31P- and 1H-NMR of the product are identical with those of Example B1.; Example B19: Reaction schemeReaction mixture 1 : 4 ml (10 mmol) of n-BuLi (2.5 M in hexane) are added dropwise to a solution of 3.44 g (10 mmol) of 1 ,1 '-dibromoferrocene in 10 ml of tetrahydrofuran (THF) at a temperature of < -30C. The mixture is stirred at this temperature for a further 30 minutes. It is then cooled to -78C and 1.36 ml (10 mmol) of phenyldichlorophosphine are added. After stirring the mixture for a further 10 minutes, the temperature is allowed to rise to room temperature and the mixture is stirred for another one hour.Reaction mixture 2: In a second vessel, 8.0 ml (10.4 mmol) of S-BuLi (1.3 M in cyclohexane) are added dropwise to a solution of 2.57 g (10 mmol) of (R)-1-dimethylamino-1-ferrocenyl- ethane in 15 ml of diethyl ether at <-10C. After stirring the mixture at the same temperature for 10 minutes, the temperature is allowed to rise to 0C and the mixture is stirred for another 1.5 hours.The reaction mixture 1 is slowly added to the reaction mixture 2 at a temperature below -10C. The mixture is subsequently stirred at room temperature for 1.5 hours. At a temperature in the range from -78C to -50C, 8 ml (10.4 mmol) of S-BuLi (1.3 M in cyclohexane) are then added dropwise. After stirring the mixture at -78C for 20 minutes, the temperature is allowed to rise to 0C and the mixture is stirred for a further 30 minutes before 2.21 ml (10 mmol) of chloro- dicyclohexylphosphine are added at -20C. The mixture is stirred at 20C for another 20 minutes and finally at room temperature for another 1.5 hours. The work-up and thermal epimerization are carried out in a manner analogous to that described in Example B18. The compound of the formula (B1 ) is obtained in a yield of 31 %. 31P- and 1H-NMR of the product are identical with those of Example B1.; Example B20:8.5 ml (11 mmol) of S-BuLi (1.3 M in cyclohexane) are added dropwise to a solution of 2.83 g (1 1 mmol) of (R)-1 -dimethylamino-1 -ferrocenylethane in 15 ml of diethyl ether at <-10C. The cooling is then removed and the mixture is stirred at room temperature for another 2 hours. After cooling to -10C, 2.92 g (10 mmol) of the compound A3 are added and the mixture is stirred at this temperature for a further 30 minutes. The temperature is allowed to rise to room temperature and the mixture is stirred for another one hour. After addition of 10 ml of 1 N NaOH, the reaction mixture is extracted, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure on a rotary evaporator. A 1H-NMR of the residue shows that the reaction is very stereoselective and gives virtually exclusively the desired diastereomer (RC,SFC, Sp)-I -[2-(1 -dimethylaminoethyl)ferrocen-1 -yl]phenylphosphino- 1 '-dicyclohexylphosphinoferrocene. After chromatography (silica gel 60; eluent = hexane/ethyl acetate 4:1 ), this product is obtained in a yield of 37%. 31P- and 1H-NMR of the produ…

As the paragraph descriping shows that 31886-58-5 is playing an increasingly important role.

Reference£º
Patent; SOLVIAS AG; WO2007/116081; (2007); A1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.31886-58-5,(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine,as a common compound, the synthetic route is as follows.

a) Preparation of the chlorophosphine (X3)3.85 ml (5 mmol) of S-BuLi (1.3 M in cyclohexane) are added dropwise to a solution of 1.29 g (5 mmol) of (R)-1-dimethylamino-1-ferrocenylethane in 5 ml of TBME at <-20C. After stirring the mixture at the same temperature for 10 minutes, the temperature is allowed to rise to room temperature and the mixture is stirred for another 1.5 hours. The reaction mixture is then cooled to -78C and 0.62 ml (5 mmol) of dichloroisopropylphosphine is added dropwise at such a rate that the temperature does not exceed -60C. Further stirring at -78C for 30 minutes and subsequently at room temperature for one hour gives a suspension comprising the chlorophosphine X3; Example B17: Preparation of the compound (Rc,SFc,SP)-1-[2-(1-dimethylaminoethyl)ferrocen- i-yllcyclohexylphosphino-i '-bis-beta.S-d^trifluoromethylJphenyllphosphinoferrocene (B17):4 ml (10 mmol) of n-BuLi (2.5 M in hexane) are added dropwise to a solution of 3.44 g (10 mmol) of 1 ,1 '-dibromoferrocene in 10 ml of tetrahydrofuran (THF) at a temperature of < -30C. The mixture is stirred at this temperature for a further 1.5 hours to give a suspension of 1-bromo-1 '-lithioferrocene X5.In a second reaction vessel, 7.7 ml (10 mmol) of S-BuLi (1.3 M in cyclohexane) are added dropwise to a solution of 2.57 g (10 mmol) of (R)-1-dimethylamino-1-ferrocenylethane in 15 ml of TBME at <-10C. After stirring the mixture at the same temperature for 10 minutes, the temperature is allowed to rise to 0 and the mixture is stirred for another 1.5 hours. The reaction mixture is then cooled to -78C and 1.51 ml (10 mmol) of dichlorocyclohexyl- phosphine are added. Further stirring at -78C for 30 minutes and, after removal of cooling, at room temperature for another one hour gives a suspension of the chlorophosphine X4 which is subsequently added at a temperature of <-10C to the suspension of 1-bromo-1 '-lithio- ferrocene X5. The cooling is then removed and the mixture is stirred at room temperature for a further 1.5 hours. After renewed cooling to <-50C, 4 ml (10 mmol) of n-BuLi (2.5 M in hexane) are added dropwise. After the addition, the temperature is allowed to rise to 0C and the mixture is stirred for a further 30 minutes. It is then cooled to -20C and 4.63 g (10 mmol) of bis[3,5-di(trifluoromethyl)phenyl]chlorophosphine are added. The cooling is subsequently removed and the mixture is stirred at room temperature for another 1.5 hours. The reaction mixture is admixed with 1 N NaOH and extracted. The organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure on a rotary evaporator. The residue is subsequently heated at 150C for one hour. Chromatographic purification (silica gel 60; eluent = hexane/ethyl acetate 8:1 ) gives the compound B17 as a yellow solid (yield: 66%). 1H NMR (300 MHz, C6D6): delta 1.25 (d, 3H, J = 6.7 Hz), 1.00-2.29 (m, 1 1 H), 2.20 (s, 6H), 3.78 (m, 1 H), 4.02 (m, 1 H), 4.04 (s, 5H), 4.09 (m, 1 H), 4.14 (m, 1 H), 4.17 (m, 1 H), 4.21 (m, 1 H), 4.40 (m, 2H), 4.60 (m, 1 H), 7.80 (d, 2H, J = 6.8 Hz), 8.00 (d, 4H, J = 6.0 Hz). 31P NMR (121.5 MHz, C6D6): delta -27.1 (s); -14.1 (s).

31886-58-5 (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine 16212257, achiral-nitrogen-ligands compound, is more and more widely used in various.

Reference£º
Patent; SOLVIAS AG; WO2007/116081; (2007); A1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

31886-58-5, (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine is a chiral-nitrogen-ligands compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of (R)-Ugi?s amine 3 (2.57 g, 10 mmol) in TBME (20 mL) was added 1.6 M t-BuLi solution in n-hexane (6.8 mL, 10.88 mmol) at 0 C. After the addition was complete, the mixture was warmed to room temperature, and stirred for 1.5 h at room temperature. The mixture was then cooled to 0 C again, and Ar2PCl (11 mmol) was added in one portion. After stirring for 20 min at 0 C, the mixture was warmed to room temperature, and stirred for 1.5 h at room temperature. The mixture was then quenched by the addition of saturated NaHCO3 solution (20 mL). The organic layer was separated and dried over MgSO4, and the solvent was removed under reduced pressure, after which the filtrate was concentrated. The residue was purified by chromatography to afford 4a, 4e, and 4f.

The synthetic route of 31886-58-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Nie, Huifang; Zhou, Gang; Wang, Quanjun; Chen, Weiping; Zhang, Shengyong; Tetrahedron Asymmetry; vol. 24; 24; (2013); p. 1567 – 1571;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.31886-58-5,(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine,as a common compound, the synthetic route is as follows.

General procedure: To a solution of (R)-Ugi?s amine 3 (2.57 g, 10 mmol) in TBME (20 mL) was added 1.6 M t-BuLi solution in n-hexane (6.8 mL, 10.88 mmol) at 0 C. After the addition was complete, the mixture was warmed to room temperature, and stirred for 1.5 h at room temperature. The mixture was then cooled to 0 C again, and Ar2PCl (11 mmol) was added in one portion. After stirring for 20 min at 0 C, the mixture was warmed to room temperature, and stirred for 1.5 h at room temperature. The mixture was then quenched by the addition of saturated NaHCO3 solution (20 mL). The organic layer was separated and dried over MgSO4, and the solvent was removed under reduced pressure, after which the filtrate was concentrated. The residue was purified by chromatography to afford 4a, 4e, and 4f.

The synthetic route of 31886-58-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Nie, Huifang; Zhou, Gang; Wang, Quanjun; Chen, Weiping; Zhang, Shengyong; Tetrahedron Asymmetry; vol. 24; 24; (2013); p. 1567 – 1571;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

31886-58-5, (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine is a chiral-nitrogen-ligands compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

500 mg (R)-N,N-dimethylferrocene amine (shown in formula a) is added to the ether solution to dissolve, and the reaction system is cooled to At -78 , add 1.2eq n-butyllithium, 1.2eqTMEDA, 1.1eq elemental iodine, react at low temperature for 30 minutes, naturally rise to room temperature, detect the reaction by TLC, quench the reaction after the reaction is completed, ethyl acetate extraction, concentration, column Chromatographic separation yields the target product (represented by formula b).Dissolve 480 mg of the obtained product in tetrahydrofuran, add 12 mg of palladium metal catalyst and 100 mg of pyridine boric acid, react at room temperature, and check the reaction after 4 hours. After the reaction is complete, directly concentrate through the column to separate. In the method, 450 mg of diphenylphosphinomethanamine was added, and the reaction was refluxed for 2 hours. The reaction was detected by TLC, and finally the target product (represented by Formula A1) was obtained, with a total yield of 31%.

As the paragraph descriping shows that 31886-58-5 is playing an increasingly important role.

Reference£º
Patent; Jiangsu Pharmaceutical Profession College; Qi Liang; Lin Rui; (8 pag.)CN110845547; (2020); A;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.31886-58-5,(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine,as a common compound, the synthetic route is as follows.

(S)-Ugi-amine 1 (2.57 g, 10 mmol) was dissolved in 25 mL of diethyl ether, and n-butyllithium (8 mL, 2.5 mol/L) was added dropwise to the reaction system under nitrogen protection and ice salt bath cooling. After that, the temperature was slowly raised to room temperature, and the reaction was stirred for 3 hours. To the ice salt bath, chlorobis(3,5-di-t-butylphenyl)phosphine (8.90 g, 20 mmol) was added dropwise thereto, and after the completion of the dropwise addition, the mixture was slowly warmed to room temperature, and the reaction was stirred for 24 hours. The reaction was quenched with saturated sodium bicarbonate solution and extracted with dichloromethane. Dry over anhydrous sodium sulfate, Concentration and column chromatography gave product 7 (3.79 g, 57%).

31886-58-5 (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine 16212257, achiral-nitrogen-ligands compound, is more and more widely used in various.

Reference£º
Patent; Zhejiang University of Technology; Zhong Weihui; Ling Fei; Nian Sanfei; (14 pag.)CN108774271; (2018); A;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.31886-58-5,(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine,as a common compound, the synthetic route is as follows.

(1) Raw material storage tanks 1,4 are respectively methyl tert-butyl ether solution of N,N-dimethyl-(R)-1-[(S)-ferrocenyl]ethylamine (mass fraction 15%) And n-hexane solution of n-butyllithium (2.7M), methyl t-butyl group of N,N-dimethyl-(R)-1-[(S)-ferrocenyl]ethylamine was controlled by a metering pump the flow rate of the ether solution was 50 mL/min, the flow rate of the n-hexane solution of n-butyllithium was 14 mL/min, and the thermostatic module injected into the microchannel reactor was thermostated at 25 C; after constant temperature treatment, the first mixing module of the microchannel reactor was introduced. The reaction was carried out at a reaction temperature of 25 C and a residence time of 10.7 s.(2) reacting the effluent of the first mixing module with diphenylphosphine chloride in a second mixing module, controlling the flow rate of diphenylphosphonium chloride to 7 mL/min by a metering pump, and the reaction temperature is 35 C, and residence time 9.8s.(3) The effluent of the microchannel reactor was acidified to neutral with concentrated hydrochloric acid, extracted with ethyl acetate, dried over anhydrous sodium sulfate and evaporated to give a brown solid N,N-dimethyl-(R)-1- [(S)-2-(diphenylphosphino)ferrocenyl]ethylamine crude,Recrystallization from ethanol gave a pale yellow solid N,N-dimethyl-(R)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine, N,N-dimethyl The mass ratio of the crude -(R)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine to ethanol was 1:5; the yield was 82.4%.

As the paragraph descriping shows that 31886-58-5 is playing an increasingly important role.

Reference£º
Patent; Xi’an Modern Chemical Institute; Yang Cuifeng; Chen Tao; Xu Zegang; Mao Mingzhen; Zhang Xiaoguang; Ning Binke; Su Tianduo; Li Bingbo; Wang Yuemei; Wei Tianqi; Zhang Yuanyuan; (7 pag.)CN108456235; (2018); A;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

31886-58-5, (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine is a chiral-nitrogen-ligands compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

15.4 ml of a cyclohexane solution of s-butyllithium (1.3 M, 22 mmol) are added to a solution of 5.14 g (20 mmol) of (R)-N, N-dimethyl-1 -ferrocenylethylamine [(R)-ugi- amine] in 30 ml of t-butyl methyl ether (TBME) at <20C over a period of 10 minutes. The mixture is then heated to 00C while stirring and maintained at this temperature for 1.5 hours. It is then cooled to <60C and 3.0 ml (20 mmol) of dichlorocyclohexyl- phosphine are added over a period of 10 minutes. After stirring at -78C for30 minutes, the mixture is allowed to warm slowly to room temperature and is stirred at this temperature for 1.5 hours. 31886-58-5 (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine 16212257, achiral-nitrogen-ligands compound, is more and more widely used in various. Reference£º
Patent; SOLVIAS AG; WO2008/55942; (2008); A1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis