(2S)-ethyl N¹-benzyl-4-oxopyrrolidine-2-carboxylate

Base Information

• Chemical Name: (2S)-ethyl N¹-benzyl-4-oxopyrrolidine-2-carboxylate
• CAS No.: 154342-89-9
• Molecular Formula: C₁₄H₁₇NO₃
• Molecular Weight: 247.294
• Mol file: 154342-89-9.mol

Synonyms:(2S)-ethyl N¹-benzyl-4-oxopyrrolidine-2-carboxylate

Chemical Property of (2S)-ethyl N¹-benzyl-4-oxopyrrolidine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-ethyl N¹-benzyl-4-oxopyrrolidine-2-carboxylate

There total 7 articles about (2S)-ethyl N¹-benzyl-4-oxopyrrolidine-2-carboxylate 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: 96.0%

(2S,4R)-ethyl N1-benzyl-4-hydroxypyrrolidine-2-carboxylate (154342-88-8) → (2S)-ethyl N1-benzyl-4-oxopyrrolidine-2-carboxylate (154342-89-9)

Guidance literature:

(2S,4R)-ethyl N¹-benzyl-4-hydroxypyrrolidine-2-carboxylate; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.75h;

With triethylamine; In dichloromethane; at -78 - 20 ℃;

Reference yield:

(2S,4R)-ethyl N1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylate (103667-57-8) → (2S)-ethyl N1-benzyl-4-oxopyrrolidine-2-carboxylate (154342-89-9)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / 5percent Pd/C / ethanol / 2.5 h / 3102.9 Torr / Ambient temperature

2: i-Pr₂NEt / ethanol / Ambient temperature

3: 94 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 2 h / -78 °C

With oxalyl dichloride; hydrogen; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1021/jm9601765

Reference yield:

(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (13504-85-3) → (2S)-ethyl N1-benzyl-4-oxopyrrolidine-2-carboxylate (154342-89-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / Et₃N / acetonitrile / 55 °C

2: H₂ / 5percent Pd/C / ethanol / 2.5 h / 3102.9 Torr / Ambient temperature

3: i-Pr₂NEt / ethanol / Ambient temperature

4: 94 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 2 h / -78 °C

With oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In ethanol; dichloromethane; acetonitrile;

DOI:10.1021/jm9601765

upstream raw materials:

(2S,4R)-ethyl N¹-benzyl-4-hydroxypyrrolidine-2-carboxylate

4R-4-hydroxyproline

(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid ethyl ester

(2S,4R)-ethyl N¹-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylate

Downstream raw materials:

(S)-7-Benzyl-2,4-dioxo-1,3,7-triaza-spiro[4.4]nonane-8-carboxylic acid ethyl ester

(2S,4S)-4-amino-1-benzyl-4-carboxyproline

(2S,4R)-4-amino-1-benzyl-4-carboxyproline

(2S,4S)-1-Benzyl-4-tert-butoxycarbonylamino-pyrrolidine-2,4-dicarboxylic acid diethyl ester

Refernces

• 1、 -. "TRANS PYRROLIDINYL DERIVATIVES AND THEIR PHARMACEUTICAL USE". Page/Page column 42-43. . Retrieved 2010/02/15.
• 2、 Tanaka,Sawanishi. "Asymmetric syntheses of all four isomers of 4-amino-4-carboxyproline: Novel conformationally restricted glutamic acid analogues". . p. 1641 - 1656. Retrieved 2007/10/02.