(2R,3S)-3-hydroxy-2-methyl-2-(2-methylphenyl)-3-phenylpropanenitrile

Base Information

• Chemical Name: (2R,3S)-3-hydroxy-2-methyl-2-(2-methylphenyl)-3-phenylpropanenitrile
• CAS No.: 960595-23-7
• Molecular Formula: C₁₇H₁₇NO
• Molecular Weight: 251.328
• Mol file: 960595-23-7.mol

Synonyms:(2R,3S)-3-hydroxy-2-methyl-2-(2-methylphenyl)-3-phenylpropanenitrile

Chemical Property of (2R,3S)-3-hydroxy-2-methyl-2-(2-methylphenyl)-3-phenylpropanenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3-hydroxy-2-methyl-2-(2-methylphenyl)-3-phenylpropanenitrile

There total 3 articles about (2R,3S)-3-hydroxy-2-methyl-2-(2-methylphenyl)-3-phenylpropanenitrile 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:

1-(1,1-dimethylethyl)-N-[2-(2-methylphenyl)-1-propenylidene]-1,1-dimethylsilanamine (960595-41-9) + benzaldehyde (100-52-7) → (2R,3S)-3-hydroxy-2-methyl-2-(2-methylphenyl)-3-phenylpropanenitrile (960595-23-7) + (2S,3R)-3-hydroxy-2-methyl-2-(2-methylphenyl)-3-phenylpropanenitrile + C17H17NO

Guidance literature:

1-(1,1-dimethylethyl)-N-[2-(2-methylphenyl)-1-propenylidene]-1,1-dimethylsilanamine; benzaldehyde; With tetrachlorosilane; chiral bisphosphoramide catalyst; In dichloromethane; at -78 ℃; for 2h;

With potassium fluoride; sodium hydrogencarbonate; In dichloromethane; at 20 ℃; for 3h; Further stages. Title compound not separated from byproducts.;

DOI:10.1021/ja077134y

Reference yield:

1-(1,1-dimethylethyl)-N-[2-(2-methylphenyl)-1-propenylidene]-1,1-dimethylsilanamine (960595-41-9) + benzaldehyde (100-52-7) → (2R,3S)-3-hydroxy-2-methyl-2-(2-methylphenyl)-3-phenylpropanenitrile (960595-23-7) + (2S,3R)-3-hydroxy-2-methyl-2-(2-methylphenyl)-3-phenylpropanenitrile + 3-hydroxy-2-methyl-2-(2-methylphenyl)-3-phenylpropanenitrile

Guidance literature:

benzaldehyde; With tetrachlorosilane; Denmark's dimeric catalyst; In dichloromethane; at -78 ℃; for 0.0833333h; Inert atmosphere; Schlenk technique;

1-(1,1-dimethylethyl)-N-[2-(2-methylphenyl)-1-propenylidene]-1,1-dimethylsilanamine; In dichloromethane; at -78 ℃; for 2.08333h; Overall yield = 74 %; Overall yield = 187 mg; stereoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.201403342

Reference yield:

2-(2-methylphenyl)propanenitrile (58422-60-9) → (2R,3S)-3-hydroxy-2-methyl-2-(2-methylphenyl)-3-phenylpropanenitrile (960595-23-7) + (2S,3R)-3-hydroxy-2-methyl-2-(2-methylphenyl)-3-phenylpropanenitrile + 3-hydroxy-2-methyl-2-(2-methylphenyl)-3-phenylpropanenitrile

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

upstream raw materials:

1-(1,1-dimethylethyl)-N-[2-(2-methylphenyl)-1-propenylidene]-1,1-dimethylsilanamine

benzaldehyde

2-(2-methylphenyl)propanenitrile

Downstream raw materials:

(1S,2R)-2-cyano-1-phenyl-2-(2-methylphenyl)propyl-3,5-dinitrobenzoate