(2R,3S)-3-hydroxy-2-(4-methoxyphenyl)-2-methyl-3-phenylpropanenitrile

Base Information

• Chemical Name: (2R,3S)-3-hydroxy-2-(4-methoxyphenyl)-2-methyl-3-phenylpropanenitrile
• CAS No.: 960595-22-6
• Molecular Formula: C₁₇H₁₇NO₂
• Molecular Weight: 267.327
• Mol file: 960595-22-6.mol

Synonyms:(2R,3S)-3-hydroxy-2-(4-methoxyphenyl)-2-methyl-3-phenylpropanenitrile

Chemical Property of (2R,3S)-3-hydroxy-2-(4-methoxyphenyl)-2-methyl-3-phenylpropanenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3-hydroxy-2-(4-methoxyphenyl)-2-methyl-3-phenylpropanenitrile

There total 3 articles about (2R,3S)-3-hydroxy-2-(4-methoxyphenyl)-2-methyl-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: 90.0%

1-(1,1-dimethylethyl)-N-[2-(4-methoxyphenyl)-1-propenylidene]-1,1-dimethylsilanamine (960595-40-8) + benzaldehyde (100-52-7) → (2R,3S)-3-hydroxy-2-(4-methoxyphenyl)-2-methyl-3-phenylpropanenitrile (960595-22-6) + C17H17NO2

Guidance literature:

1-(1,1-dimethylethyl)-N-[2-(4-methoxyphenyl)-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.;

DOI:10.1021/ja077134y

Reference yield: 90.0%

1-(1,1-dimethylethyl)-N-[2-(4-methoxyphenyl)-1-propenylidene]-1,1-dimethylsilanamine (960595-40-8) + benzaldehyde (100-52-7) → (2R,3S)-3-hydroxy-2-(4-methoxyphenyl)-2-methyl-3-phenylpropanenitrile (960595-22-6)

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-(4-methoxyphenyl)-1-propenylidene]-1,1-dimethylsilanamine; In dichloromethane; at -78 ℃; for 2.08333h; stereoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.201403342

Reference yield:

2-(4-methoxyphenyl)propionitrile (31007-06-4) → (2R,3S)-3-hydroxy-2-(4-methoxyphenyl)-2-methyl-3-phenylpropanenitrile (960595-22-6)

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-(4-methoxyphenyl)-1-propenylidene]-1,1-dimethylsilanamine

benzaldehyde

2-(4-methoxyphenyl)propionitrile

Refernces

• 1、 Denmark, Scott E.,Wilson, Tyler W.,Burk, Matthew T.,Heemstra Jr., John R.. "Enantioselective construction of quaternary stereogenic carbons by the Lewis base catalyzed additions of silyl ketene imines to aldehydes". . p. 14864 - 14865. Retrieved 2008/09/18.