Day: September 11, 2020

Name is N1,N2-Dimethylethane-1,2-diamine, as a common heterocyclic compound, it belongs to chiral-nitrogen-ligands compound, and cas is 110-70-3, its synthesis route is as follows.,110-70-3

Preparation of Methyl-(2-methylamino-ethyl)-carbamic acid tert-butyl esterTo an ice-cooled solution of N,N’-dimethyethylenediamine (10 ml_, 91.0 mmol) in dry THF (150 ml.) was added a solution of BoC2O (4.97 g, 22.8 mmol) in dry THF (50 ml.) over 30 minutes. The reaction mixture was stirred for 1 h at 00C then at rt overnight, and concentrated in vacuo. The resulting residue was taken up in a mixture of EA and a sat.NH4CI solution. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. FC (10 % MeOH in DCM) afforded the title compound as a yellow oil (2.90 g, 17%). LC-MS (analytic A, Zorbax SB-AQ column, acidic conditions): tR = 0.50 min; [M+H]+ 189.40.

With the complex challenges of chemical substances, we look forward to future research findings about N1,N2-Dimethylethane-1,2-diamine

Reference£º
Patent; ACTELION PHARMACEUTICALS LTD; AISSAOUI, Hamed; BOSS, Christoph; CORMINBOEUF, Olivier; FRANTZ, Marie-Celine; GRISOSTOMI, Corinna; WO2010/58353; (2010); 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

Name is Tris[2-(dimethylamino)ethyl]amine, as a common heterocyclic compound, it belongs to chiral-nitrogen-ligands compound, and cas is 33527-91-2, its synthesis route is as follows.,33527-91-2

General procedure: The copper complex Cu5-1 was dissolved in water, and an excessive amount of an aqueous solution of saturated sodium tetrafluoroborate (manufactured by Wako Pure Chemical Industries, Ltd.) was added while stirring. A precipitated solid was collected by filtering and a copper complex Cu5-72 was obtained.

With the complex challenges of chemical substances, we look forward to future research findings about Tris[2-(dimethylamino)ethyl]amine

Reference£º
Patent; FUJIFILM Corporation; Sasaki, Kouitsu; Kawashima, Takashi; Hitomi, Seiichi; Shiraishi, Yasuharu; US10215898; (2019); B2;,
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

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

b) Preparation of A1 (Mixture of Diastereomers); 15.5 ml (23.2 mmol) of t-butyllithium (t-BuLi) (1.5 M in pentane) are added dropwise to a solution of 5.98 g (23.2 mmol) of (R)-1-dimethylamino-1-ferrocenylethane in 40 ml of DE at <-10 C. After stirring for 10 minutes at the same temperature, the temperature is allowed to rise to room temperature and the mixture is stirred for another 1.5 hours. This gives a solution of the compound X2 which is added via a cannula to the cooled suspension of the monochlorophosphine X1 at such a rate that the temperature does not exceed -30 C. After stirring at -30 C. for a further 10 minutes, the temperature is allowed to rise to 0 C. and the mixture is stirred at this temperature for another 2 hours. The reaction mixture is admixed with 20 ml of water. The organic phase is separated off, dried over sodium sulphate and the solvent is distilled off under reduced pressure on a rotary evaporator. Purification by chromatography (silica gel 60; eluent=heptane/EtOAc/Et3N 85:10:5) gives 11.39 g of the desired product as a mixture of 2 diastereomers. With the complex challenges of chemical substances, we look forward to future research findings about (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine Reference£º
Patent; Chen, Weiping; Spindler, Felix; Nettekoven, Ulrike; Pugin, Benoit; US2010/160660; (2010); 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

Name is Tris[2-(dimethylamino)ethyl]amine, as a common heterocyclic compound, it belongs to chiral-nitrogen-ligands compound, and cas is 33527-91-2, its synthesis route is as follows.,33527-91-2

General procedure: The copper complex Cu5-1 was dissolved in water, and an excessive amount of an aqueous solution of saturated sodium tetrafluoroborate (manufactured by Wako Pure Chemical Industries, Ltd.) was added while stirring. A precipitated solid was collected by filtering and a copper complex Cu5-72 was obtained.

With the complex challenges of chemical substances, we look forward to future research findings about Tris[2-(dimethylamino)ethyl]amine

Reference£º
Patent; FUJIFILM Corporation; Sasaki, Kouitsu; Kawashima, Takashi; Hitomi, Seiichi; Shiraishi, Yasuharu; US10215898; (2019); B2;,
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

Name is 3,4-Di(1H-indol-3-yl)-1H-pyrrole-2,5-dione, as a common heterocyclic compound, it belongs to chiral-nitrogen-ligands compound, and cas is 119139-23-0, its synthesis route is as follows.,119139-23-0

EXAMPLE 14 820 mg of Lawesson’s reagent was added to a solution of 330 mg of 3,4-bis(3-indolyl)-1H-pyrrole-2,5-dione in 50 ml of dimethoxyethane and the mixture was heated to reflux for 1 hour. 410 mg of Lawesson’s reagent were then added and the mixture was heated to reflux for a further 1 hour. The solvent was evaporated and the residue was purified on silica gel with ethyl acetate/hexane (1:4). Recrystallization from diethyl ether/hexane gave 30 mg of 5-thioxo-3,4-bis(3-indolyl)-3-pyrrolin-2-one, m.p. 254-257 C.

With the complex challenges of chemical substances, we look forward to future research findings about 3,4-Di(1H-indol-3-yl)-1H-pyrrole-2,5-dione

Reference£º
Patent; Hoffmann-La Roche Inc.; US5057614; (1991); 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

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

EXAMPLE A2; Preparation of (RC,SFc,SP)-1-[2-(1-dimethylaminoethyl)ferrocen-1-yl]cyclo-hexylphosphino-1′-bromoferrocene of the formula (A2) [Cy=cyclohexyl; Me=methyl]; a) Preparation of the Monochlorophosphine X4; 1.3 M s-BuLi solution in cyclohexane (7.7 ml, 10 mmol) is added to a solution of (R)-N,N-dimethyl-1-ferrocenylethylamine[(R)-Ugi amine] (2.57 g, 10 mmol) in TBME (15 ml) over a period of 10 minutes and at a temperature below -20 C. After the addition is complete, the reaction mixture is warmed to 0 C. and stirred at this temperature for 1.5 hours. Dichlorocyclohexylphosphine (1.51 ml, 10 mmol) is then added at a temperature below -60 C. over a period of 10 minutes. The mixture is then stirred at -78 C. for another 30 minutes, the cooling bath is removed, the reaction mixture is stirred for a further one hour. This gives the monochlorophosphine X4.; EXAMPLE 1; Preparation of [(RC,RC,)(SFc,SFc,)(SP,SP)-1-[2-(1-dimethylaminoethyl)ferrocenyl]phenylphosphino-1′-[2-(1-dimethylaminoethyl)ferrocenyl]cyclohexylphosphinoferrocene of the formula (B1) [R=phenyl; Me=methyl, R’=cyclohexyl]; Reaction mixture a) 1.3 M s-BuLi solution in cyclohexane (3.85 ml, 5 mmol) is added to a solution of (R)-N,N-dimethyl-1-ferrocenylethylamine[(R)-Ugi amine] (1.28 g, 5 mmol) in TBME (10 ml) over a period of 10 minutes and at a temperature below -20 C. After the addition is complete, the reaction mixture is warmed to 0 C. and stirred at this temperature for another 1.5 hours. Dichlorocyclohexylphosphine (0.76 ml, 5 mmol) is then added at a temperature below -60 C. over a period of 10 minutes. The reaction mixture is then stirred at -78 C. for another 30 minutes, the cooling bath is removed and the reaction mixture is stirred for a further one hour to give the monochlorophosphine X7.; EXAMPLE 3; Preparation of [(RC,RC,)(SFc,SFc,)(SP,SP)-1-[2-(1-dimethylaminoethyl)-ferrocenyl]phenylphosphino-1′-[2-(1-dimethylaminoethyl)ferrocenyl]cyclohexyl-phosphinoferrocene of the formula (B1) [R=phenyl; Me=methyl, R’=cyclohexyl]; a) 1.3 M s-BuLi solution in cyclohexane (3.85 ml, 5 mmol) is added to a solution of (R)-N,N-dimethyl-1-ferrocenylethylamine[(R)-Ugi amine] (1.28 g, 5 mmol) in TBME (10 ml) over a period of 10 minutes and at a temperature below -20 C. After the addition is complete, the reaction mixture is warmed to 0 C. and stirred at this temperature for another 1.5 hours. This gives the lithiated Ugi amine X9.; EXAMPLE 4; Preparation of [(RC,RC,)(SFc,SFc,)(SP,SP)-1-[2-[(1-dimethylaminoethyl)-ferrocenyl]phenylphosphino-1′-[2-(1-dimethylaminoethyl)ferrocenyl]isopropyl-phosphinoferrocene of the formula (B2) [R=phenyl; Me=methyl, R’=isopropyl]; a) 1.3 M s-BuLi solution in cyclohexane (3.08 ml, 4 mmol) is added to a solution of (R)-N,N-dimethyl-1-ferrocenylethylamine[(R)-Ugi amine] (1.03 g, 4 mmol) in TBME (10 ml) over a period of 10 minutes and at a temperature below -20 C. After the addition is complete, the reaction mixture is warmed to 0 C. and stirred at this temperature for another 1.5 hours. This gives the lithiated Ugi amine X9.; b) In a vessel, 7.7 ml (10 mmol) of s-BuLi (1.3 M in cyclohexane) are added to a solution of (R)-N,N-dimethyl-1-ferrocenylethylamine[(R)-Ugi amine] (2.57 g, 10 mmol) in TBME (15 ml) at a temperature below -20 C. over a period of 10 minutes. After the addition is complete, the reaction mixture is warmed to 0 C. and stirred at this temperature for another 1.5 hours. Dichloroisopropylphosphine (1.23 ml, 10 mmol) is then added at a temperature below -60 C. over a period of 10 minutes. The mixture is then stirred at -78 C. for another 30 minutes, the cooling bath is removed and the reaction mixture is stirred for a further one hour. This gives the monochlorophosphine X8.; EXAMPLE ; Preparation of [(RC,RC),(SFc,SFc),(SP,SP)]-1-[2-(1-N,N-dimethylamino-ethyl)-1-ferrocenyl](4-methoxyphenyl)phosphino-1′-[2-(1-N,N-dimethylaminoethyl)-1-ferrocenyl]cyclohexylphosphinoferrocene of the formula (B6); Reaction mixture a): 7.7 ml (10 mmol) of s-BuLi (1.3 M in cyclohexane) are added dropwise to a cooled solution of 2.57 g (10 mmol) of (R)-N,N-dimethyl-1-ferrocenyl-ethylamine [(R)-Ugi amine] in TBME (15 ml) at such a rate that the temperature remains below -20 C. After the addition, the temperature is allowed to rise to 0 C. and the mixture is stirred at this temperature for another 1.5 hours. The mixture is then cooled to -78 C. and 1.52 ml (10 mmol) of cyclohexyldichlorophosphine are added dropwise at such a rate that the temperature does not exceed -60 C. The mixture is stirred at -78 C. for a further 30 minutes, the cooling is then removed and the suspension containing the monochlorophosphine (RC,SFc)-[2-(1-N,N-dimethylamino-ethyl)-1-ferrocenyl]cyclohexylchlorophosphine is stirred for a further 1 hour.; Reaction mixture d): 7.7 ml (10 mmol) of s-BuLi (1.3 M in cyclohexane) are added dropwise to a cooled solution of (R)-N,N-dimethyl-1-ferrocenylethylamine[(R)-Ugi amine] (2.57 g, 10 mmol) in TBME (15 ml) at such a rate th…

With the complex challenges of chemical substances, we look forward to future research findings about (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine

Reference£º
Patent; Chen, Weiping; Spindler, Felix; Nettekoven, Ulrike; Pugin, Benoit; US2010/160660; (2010); 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

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

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.

With the complex challenges of chemical substances, we look forward to future research findings about (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine

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

Name is N1,N2-Dimethylethane-1,2-diamine, as a common heterocyclic compound, it belongs to chiral-nitrogen-ligands compound, and cas is 110-70-3, its synthesis route is as follows.,110-70-3

Example 71Synthesis of tert-butyl methyl [2-(methylamino)ethyl]carbamate (VI-I) A solution of di-tert-butyl dicarbonate (2.18 g, 0.01 mol) in CH2Cl2 (120 mL) was added dropwise to a solution of N,N’-Dimethyl-ethane-1,2-diamine (1.76 g, 0.02 mol) in CH2Cl2 (40 mL) over 6 h with vigorous stirring. The reaction mixture was continued to stir for a further 18 h at room temperature. Then the solvent was concentrated in vacuo to give an oily residue, which was dissolved in 60 mL of 2M Na2CO3 aqueous solution, and extracted with CH2Cl2 (30 mL x 2). The combined organic layers were washed with 2M Na2CO3 (30 mL x 2), and dried over anhydrous MgSO4. The solvent was evaporated in vacuo to yield the product, which was purified by column chromatography (silica gel, CH2Cl2 : MeOH, 9: 1) to afford colorless oil (VI-I, 1.15 g, 61%)

With the complex challenges of chemical substances, we look forward to future research findings about N1,N2-Dimethylethane-1,2-diamine

Reference£º
Patent; NORTHWESTERN UNIVERSITY; SILVERMAN, Richard, B.; JI, Haitao; LAWTON, Graham, R.; WO2008/42353; (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

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

b) Preparation of L (mixture of diastereomers).At <-100C, 15.5 ml (23.2 mmol) of t-butyllithium (t-Bu-Li) (1.5 M in pentane) are added dropwise to a solution of 5.98 g (23.2 mmol) of (R)-1 -dimethylamino-1 - ferrocenylethane in 40 ml of diethyl ether (DE). After stirring 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. A solution of the compound X2 is thus obtained, which is added via a cannula to the cooled suspension of the monochlorophosphine X1 at a sufficiently slow rate that the temperature does not exceed -300C. After stirring at -30C for a further 10 minutes, the temperature is allowed to rise to 0C, and the mixture is stirred at this temperature for another 2 hours. The reaction mixture is admixed with 20 ml of water. The organic phase is removed and dried over sodium sulphate, and the solvent is distilled off on a rotary evaporator under reduced pressure. After chromatographic purification (silica gel 60; eluent = heptane/ethyl acetate(EA)/Nethyl3(Net3) 85:10:5), 11.39 g of the desired product are obtained as a mixture of 2 diastereomers. With the complex challenges of chemical substances, we look forward to future research findings about (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine Reference£º
Patent; SPEEDEL EXPERIMENTA AG; WO2008/113835; (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

N1,N2-Dimethylethane-1,2-diamine, cas is 110-70-3, it is a common heterocyclic compound, the chiral-nitrogen-ligands compound, its synthesis route is as follows.,110-70-3

The above mentioned protocol was adapted for preparation ofligand L2. In a solution of 2-(chloromethyl)-3,4-dimethoxypyridinehydrochloride (2.09 g, 9.34 mmol) in 10 mL of water, a solution ofpotassium bicarbonate(2.73 g, 19.74 mmol) in water (10 mL) wasadded dropwise. The reaction mixture was stirred at room temperaturefor next 30 min. After stirring is done, solution was extractedwith dichloromethane (3 20 mL). The combined dichloromethanelayer was treated with anhydrous sodium sulfate. Thesolution was filtered and solvent was removed by rotatory evaporation.The collected light yellow oil was dissolved in dichloromethane(10 mL). The 2-(chloromethyl)-3,4-dimethoxypyridinesolution in dichloromethane was added dropwise to a solution of N,N0-dimethylethylenediamine (0.503 mL, 4.67 mmol) in dichloromethane(15 mL). In the next step aqueous 1 M sodium hydroxide(10 mL) was slowly added and solution was stirred for additional60 h at room temperature. After 60 h of stirring followed by therapid addition of a second fraction of aqueous 1 M sodium hydroxide(10 mL, 10 mmol), the product was extracted with dichloromethane(3 25 mL). The combined organic layers were driedover anhydrous sodium sulfate and filtered. Subsequently, theexcess solvent was evaporated by vacuum to afford yellow colorviscous oil (1.86 g, Yield 89%). 1H NMR (500 MHz, Methanol-d4) d8.14 (d, 2H, pyridine ring), 7.05 (d, 2H, pyridine ring), 3.95 (s,6H,-O-CH3-Py), 3.85 (s, 6H,-O-CH3-Py), 3.66 (s, 4H,-N-CH2-Py),2.67 (s, 4H, -CH2-CH2-), 2.26 (s, 6H, -N-CH3). 13C NMR (126 MHz,Methanol-d4) d 160.77, 152.19, 147.28, 146.07 (d, J = 10.3 Hz),108.87, 61.40, 58.17, 56.43, 56.07, 43.10. ESI-MS (in CH3OH).observed m/z 391.3 [(L2 + H)+] (z = 1); theoretical-391.23[(L2 + H)+] (z = 1). IR (cm1): 3375, 2945, 1626, 1584, 1447, 1425,1261, 1228, 1173, 1073, 994, 828, 651, 603.

110-70-3 is used more and more widely, we look forward to future research findings about N1,N2-Dimethylethane-1,2-diamine

Reference£º
Article; Singh, Nirupama; Niklas, Jens; Poluektov, Oleg; Van Heuvelen, Katherine M.; Mukherjee, Anusree; Inorganica Chimica Acta; vol. 455; (2017); p. 221 – 230;,
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