(2R,3S)-3-hydroxy-2-methyl-2-phenyl-3-(4-trifluoromethylphenyl)propanenitrile

Base Information

Chemical Name:(2R,3S)-3-hydroxy-2-methyl-2-phenyl-3-(4-trifluoromethylphenyl)propanenitrile
CAS No.:960595-33-9
Molecular Formula:C₁₇H₁₄F₃NO
Molecular Weight:305.299
Hs Code.:

Synonyms:(2R,3S)-3-hydroxy-2-methyl-2-phenyl-3-(4-trifluoromethylphenyl)propanenitrile

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Chemical Property of (2R,3S)-3-hydroxy-2-methyl-2-phenyl-3-(4-trifluoromethylphenyl)propanenitrile

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Technology Process of (2R,3S)-3-hydroxy-2-methyl-2-phenyl-3-(4-trifluoromethylphenyl)propanenitrile

There total 5 articles about (2R,3S)-3-hydroxy-2-methyl-2-phenyl-3-(4-trifluoromethylphenyl)propanenitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

: 455-19-6
4-Trifluoromethylbenzaldehyde

: 53097-53-3
1-(2,3-dimethylbutan-2-yl)-1,1-dimethyl-N-(2-phenylprop-1-en-1-ylidene)silanamine

: 960595-33-9
(2R,3S)-3-hydroxy-2-methyl-2-phenyl-3-(4-trifluoromethylphenyl)propanenitrile

Guidance literature:: 4-Trifluoromethylbenzaldehyde; 1-(2,3-dimethylbutan-2-yl)-1,1-dimethyl-N-(2-phenylprop-1-en-1-ylidene)silanamine; With tetrachlorosilane; chiral bisphosphoramide catalyst; In dichloromethane; at -78 ℃; for 2h;

With potassium fluoride; sodium hydrogencarbonate; In dichloromethane; at 20 ℃; for 3h; Further stages.;
DOI:10.1021/ja077134y

Reference yield:

: 455-19-6
4-Trifluoromethylbenzaldehyde

: 1200-71-1,29738-03-2,35677-21-5,29738-04-3
2-cyano-2-phenylpropionic acid

: 960595-33-9
(2R,3S)-3-hydroxy-2-methyl-2-phenyl-3-(4-trifluoromethylphenyl)propanenitrile

: 3-hydroxy-2-methyl-2-phenyl-3-(4-trifluoromethylphenyl)propionitrile

: 3-hydroxy-2-methyl-2-phenyl-3-(4-trifluoromethylphenyl)propionitrile

Guidance literature:: With ((SP)-1-[(S)-α-(dimethylamino)-2-(diphenylphosphino)benzyl]-2-diphenylphosphinoferrocene); copper (I) acetate; In tetrahydrofuran; at -25 ℃; for 12h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2011.05.108

Reference yield:

: 1823-91-2
1-phenylethyl cyanide

: 960595-33-9
(2R,3S)-3-hydroxy-2-methyl-2-phenyl-3-(4-trifluoromethylphenyl)propanenitrile

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere; Schlenk technique

1.2: 1 h / -78 - 20 °C / Inert atmosphere; Schlenk technique

2.1: Denmark's dimeric catalyst; tetrachlorosilane / dichloromethane / 0.08 h / -78 °C / Inert atmosphere; Schlenk technique

2.2: 2.08 h / -78 °C / Inert atmosphere; Schlenk technique

With n-butyllithium; tetrachlorosilane; Denmark's dimeric catalyst; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1002/chem.201403342