October 15, 2020 | Chiral nitrogen ligands

Extracurricular laboratory: Synthetic route of 110-70-3

The chemical industry reduces the impact on the environment during synthesis,110-70-3,N1,N2-Dimethylethane-1,2-diamine,I believe this compound will play a more active role in future production and life.

110-70-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. N1,N2-Dimethylethane-1,2-diamine, cas is 110-70-3,the chiral-nitrogen-ligands compound, it is a common compound, a new synthetic route is introduced below.

To 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 0 C. then at rt overnight, and concentrated in vacuo. The resulting residue was taken up in a mixture of EA and a sat. NH4Cl 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.

Reference£º
Patent; Aissaoui, Hamed; Boss, Christoph; Corminboeuf, Olivier; Frantz, Marie-Celine; Grisostomi, Corinna; US2011/224210; (2011); 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

The important role of 110-70-3

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of N1,N2-Dimethylethane-1,2-diamine, 110-70-3

The ligand L1 was synthesized via previously reported procedure[23]. A solution of potassium carbonate (2.55 g, 18.45 mmol)in 10 mL water was dropwise added to the aqueous solution of 2-(chloromethyl)-pyridine hydrochloride (1.5 g, 9.15 mmol in10 mL). After about 30 min. of stirring at room temperature, thereaction mixture was extracted with dichloromethane(3 20 mL). The combined organic extracts were dried over anhydroussodium sulfate. The solution was filtered and the solvent wasremoved under vacuum. The resulted residue was then dissolvedin dichloromethane (10 mL). The dichloromethane solution of 2-chloromethyl-pyridine was added dropwise to a solution of N,N0-dimethylethylenediamine (0.471 mL, 5.34 mmol) in dichloromethane(15 mL). After this addition, 10 mL of aqueous sodiumhydroxide (1 M) was added slowly and the reaction mixture wasstirred for next 60 h at room temperature. After stirring was finished,another fraction of sodium hydroxide (10 mL, 1 M) wasadded rapidly. The reaction mixture was extracted with dichloromethane(3 25 mL) and combined organic portion was dried overanhydrous sodium sulfate. Evaporation of solvent led to isolationof the ligand L1 as a dark orange oil. (1.13 g, Yield 79%) 1H NMR(500 MHz, Methanol-d4) d 7.27 (m, 2H, pyridine ring), 7.50 (d,2H, pyridine ring), 7.76 (m, 2H, pyridine ring), 8.45 (d, 2H, pyridinering), 3.68 (s, 4H, -N-CH2-Py), 2.63 (s, 4H, -CH2-CH2-), 2.26 (s, 6H,N-CH3). IR (cm1): 2945, 2789, 1589, 1569, 1472, 1432, 1360,1304, 1146, 1090, 1031, 994, 635, 614, 418.

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

Share a compound : 31886-58-5

31886-58-5, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,31886-58-5 ,(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, other downstream synthetic routes, hurry up and to see

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

(S)-Ugi-amine 1 (5.14g, 20mmol) was dissolved in 50mL of diethyl ether. Under nitrogen and ice salt bath cooling, n-butyl lithium (16mL, 2.5mol / L) was added dropwise to the reaction system, After the completion, the temperature was slowly raised to room temperature, and the reaction was stirred for 3 hours. Chlorodiphenylphosphine (8.82 g, 40 mmol) was added dropwise under ice-cooling, and the mixture was slowly warmed to room temperature and stirred for 12 hours. The reaction was quenched with saturated sodium bicarbonate solution. Extracted with dichloromethane, dried over anhydrous sodium sulfate, concentration, column chromatography to obtain compound 2 (5.38g, 61%).

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

Some tips on N1,N2-Dimethylethane-1,2-diamine

1,4-Dimethyl-3-(4-nitrophenyl)piperazin-2-one (3); A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen, charged with N1,N2-dimethylethane-1,2-diamine (1.61 g, 18.2 mmol), ethanol (5 mL) and 2 (500 mg, 1.82 mmol), and the reaction was stirred at room temperature for 1 h. After this time, the reaction mixture was evaporated under reduced pressure, and the resulting residue was purified by flash column chromatography to afford an 89% yield (404 mg) of 3 as a yellow oil: 1H NMR (500 MHz, DMSO-d6) delta 8.18 (d, 2H, J=8.5 Hz), 7.60 (d, 2H, J=8.5 Hz), 3.87 (s, 1H), 3.61 (td, 1H, J=12.0, 4.0 Hz), 3.26 (ddd, 1H, J=12.0, 4.0, 2.5 Hz), 3.02 (ddd, 1H, J=12.0, 4.0, 2.5 Hz), 2.84 (s, 3H), 2.64 (td, 1H, J=12.0, 4.0 Hz), 2.06 (s, 3H).

Reference£º
Patent; Zhao, Zhongdong; Zhichkin, Pavel E.; Stafford, Douglas G.; Kropf, Jeffrey E.; BLOMGREN, Peter A.; Currie, Kevin S.; Lee, Seung H.; Mitchell, Scott A.; Xu, Jianjun; Schmitt, Aaron C.; US2009/82330; (2009); 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

The important role of 31886-58-5

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,31886-58-5,(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine,its application will become more common.

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

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. This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,31886-58-5,(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine,its application will become more common. 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

Application of Isothiazole-4-carboxylic acid

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand Tris[2-(dimethylamino)ethyl]amine reaction routes.

33527-91-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. Tris[2-(dimethylamino)ethyl]amine, cas is 33527-91-2,the chiral-nitrogen-ligands compound, it is a common compound, a new synthetic route is introduced below.

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.

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

Share a compound : 110-70-3

110-70-3, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,110-70-3 ,N1,N2-Dimethylethane-1,2-diamine, other downstream synthetic routes, hurry up and to see

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

N, N’-Dimethylethylenediamine (5.00g, 57mmol) was dissolved in CH2Cl2 (25mL) and cooled to 0C. Di-tert-butyl dicarbonate (5.00g, 22mmol) was dissolved in CH2Cl2 (25mL) and added dropwise to the reaction flask at 0C, and then warmed to room temperature and stirred overnight. The reaction solution was quenched with H2O (20mL), and extracted with CH2Cl2 (40mL x 2), and the combined organic layers dried with Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel using CH3OH/CH2Cl2 (1/20, V/V) as eluent to give 2 as colorless oil (4.37g, 81%), 1H NMR (400MHz, CDCl3) delta 3.39-3.36 (m, 2H, CH2), 2.95-2.90 (s, 3H, CH3), 2.76 (m, 2H, CH2), 2.48 (s, 3H, CH3), 1.48 (s, 9H, (CH3)3); HRMS (ESI) m/z [M+H]+ Calcd for C9H21N2O2+: 189.1603. Found: 189.1601.

Reference£º
Article; Yang, Hao; Ouyang, Yifan; Ma, Hao; Cong, Hui; Zhuang, Chunlin; Lok, Wun-Taai; Wang, Zhe; Zhu, Xuanli; Sun, Yutong; Hong, Wei; Wang, Hao; Bioorganic and Medicinal Chemistry Letters; vol. 27; 20; (2017); p. 4635 – 4642;,
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

Analyzing the synthesis route of 110-70-3

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

To a solution of 2-thiophenecarboxaldehyde (8.6 ml, 104 mmol) in toluene was added A110-70-3, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,110-70-3 ,N1,N2-Dimethylethane-1,2-diamine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; METABASIS THERAPEUTICS, INC.; WO2009/23718; (2009); A2;,
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

Extracurricular laboratory: Synthetic route of 31886-58-5

The chemical industry reduces the impact on the environment during synthesis,31886-58-5,(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine,I believe this compound will play a more active role in future production and life.

31886-58-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, cas is 31886-58-5,the chiral-nitrogen-ligands compound, it is a common compound, a new synthetic route is introduced below.

The compound having the structure shown in Formula (II) of FIG. 4 was made using the scheme set forth in FIG. 1. First, alpha-Dimethylaminoethylferrocene, (14.30 g, 55.61 mmol), (as Compound 1) was dissolved in solvent (85 ml) under argon. N-butyl lithium (1.6 M) was added slowly (22.6 ml, 66.73 mmol, 1.2 eq.) and the reaction was stirred at room temperature for one hour. The solution was then purged with argon for thirty minutes. Chlorodiphenylphosphine (12.0 ml, 66.73 mmol, 1.2 eq.) in tert-butyl methyl ether (10 ml) was added slowly, and the reaction stirred at room temperature for four hours. The reaction was cooled to 0 C., and saturated sodium bicarbonate solution (57 ml) was added followed by water (45 ml). The composition separated into aqueous and organic phases, and the aqueous layer was removed and washed with toluene, and the resulting toluene was separated from the aqueous layer and combined with the organic layer, with the resulting composition being was dried over magnesium sulfate. The magnesium sulfate hydrate was then removed by filtration. The resulting filtrate solution was concentrated under vacuum to give an orange oil. The resulting oil was dissolved in ethanol and then solvents were removed under vacuum once more. The oil was then recrystallized by dissolving in the minimum amount of hot ethanol (45 ml) and cooling to room temperature. The resulting product, present as an orange solid, contained compound 2, which was 1-alpha-dimethyl-aminoethyl-2-(diphenylphosphino)ferrocene (9.16 g, 20.7 mmol, 31% yield).

Reference£º
Patent; Eastman Chemical Company; How, Rebecca; Clarke, Matt; Hembre, Robert Thomas; Ponasik, James A.; Tolleson, Ginette S.; (17 pag.)US9308527; (2016); 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

Share a compound : 31886-58-5

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.

The compound having the structure shown in formula (VI) of FIG. 4 was made using the scheme set forth in FIG. 2. Referring to FIG. 2, alpha-Dimethylaminoethylferrocene (as Compound 1) (0.52 g, 2.03 mmol) was dissolved in diethyl ether (8.3 ml). Next, sec-butyl lithium (2.0 ml, 1.4 M solution, 1.36 eq) was added and the mixture was stirred at room temperature overnight. Chlorobis[3,5-bis(trifluoromethyl)phenyl]phosphine (1.0 g, 2.03 mmol, 1.0 eq) in diethyl ether (1.7 ml) was added dropwise and the solution was refluxed for 5 hours. An aqueous solution saturated with sodium bicarbonate (15 ml) was added. The layers were separated and the aqueous layer washed with diethyl ether (2¡Á6 ml). The separated organic layer was combined with the diethyl ether washings and dried over magnesium sulfate. The solution was concentrated under vacuum and purified by column chromatography on alumina using 30:1 hexane:ethyl acetate as eluent. This resulted in an orange oil containing Compound 2 (0.60 g, 0.84 mmol, 41%).