((R)-3-Cyano-2-phenyl-propyl)-carbamic acid methyl ester

Base Information

• Chemical Name: ((R)-3-Cyano-2-phenyl-propyl)-carbamic acid methyl ester
• CAS No.: 321125-73-9
• Molecular Formula: C₁₂H₁₄N₂O₂
• Molecular Weight: 218.255
• Mol file: 321125-73-9.mol

Synonyms:((R)-3-Cyano-2-phenyl-propyl)-carbamic acid methyl ester

Chemical Property of ((R)-3-Cyano-2-phenyl-propyl)-carbamic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((R)-3-Cyano-2-phenyl-propyl)-carbamic acid methyl ester

There total 3 articles about ((R)-3-Cyano-2-phenyl-propyl)-carbamic acid methyl ester 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:

methanol (67-56-1) + (3S)-4-cyano-3-phenylbutanoic acid (321125-69-3) → ((R)-3-Cyano-2-phenyl-propyl)-carbamic acid methyl ester (321125-73-9)

Guidance literature:

(3S)-4-cyano-3-phenylbutanoic acid; With chloroformic acid ethyl ester; triethylamine; In acetone; at 0 ℃; for 2.5h;

With sodium azide; In water; acetone; for 2h;

methanol; for 3h; Heating;

DOI:10.1016/S0957-4166(02)00028-9

Reference yield:

3-phenylglutaronitrile (78533-73-0) → ((R)-3-Cyano-2-phenyl-propyl)-carbamic acid methyl ester (321125-73-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Rhodococcus sp. AJ₂₇₀ cells / aq. phosphate buffer; acetone / 24 h / 30 °C / pH 7.0

2.1: ClCO₂Et; Et₃N / acetone / 2.5 h / 0 °C

2.2: NaN₃ / acetone; H₂O / 2 h

2.3: 140 mg / 3 h / Heating

With Rhodococcus sp. AJ₂₇₀ cells; chloroformic acid ethyl ester; triethylamine; In phosphate buffer; acetone; 2.1: Curtius rearrangement;

DOI:10.1016/S0957-4166(02)00028-9

Reference yield:

methanol (67-56-1) + 3-phenylglutaronitrile (78533-73-0) → ((S)-3-Cyano-2-phenyl-propyl)-carbamic acid methyl ester + ((R)-3-Cyano-2-phenyl-propyl)-carbamic acid methyl ester (321125-73-9)

Guidance literature:

Multistep reaction. Title compound not separated from byproducts;

DOI:10.1016/S0040-4039(00)01518-5

upstream raw materials:

methanol

3-phenylglutaronitrile

(3S)-4-cyano-3-phenylbutanoic acid

Downstream raw materials:

(R)-Phenibut

Refernces

• 1、 Wang,Liu,Li,Meth-Cohn. "Microbial desymmetrization of 3-arylglutaronitriles, an unusual enhancement of enantioselectivity in the presence of additives". . p. 8549 - 8552. Retrieved 2007/10/03.