tert-butyl (2R,5R)-1-benzyl-5-(2-hydroxyethyl)pyrrolidine-2-carboxylate

Base Information

• Chemical Name: tert-butyl (2R,5R)-1-benzyl-5-(2-hydroxyethyl)pyrrolidine-2-carboxylate
• CAS No.: 90741-40-5
• Molecular Formula: C₁₈H₂₇NO₃
• Molecular Weight: 305.417
• Mol file: 90741-40-5.mol

Synonyms:tert-butyl (2R,5R)-1-benzyl-5-(2-hydroxyethyl)pyrrolidine-2-carboxylate

Chemical Property of tert-butyl (2R,5R)-1-benzyl-5-(2-hydroxyethyl)pyrrolidine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2R,5R)-1-benzyl-5-(2-hydroxyethyl)pyrrolidine-2-carboxylate

There total 9 articles about tert-butyl (2R,5R)-1-benzyl-5-(2-hydroxyethyl)pyrrolidine-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: 95.0%

(2R-cis)-5-((1,1-Dimethylethoxy)carbonyl)-1-(phenylmethyl)-2-pyrrolidineacetic acid methyl ester (90741-36-9) → tert-butyl (2R,5R)-1-benzyl-5-(2-hydroxyethyl)pyrrolidine-2-carboxylate (90741-40-5)

Guidance literature:

With lithium borohydride; In diethyl ether; for 4h;

DOI:10.1021/ja00328a040

Reference yield:

(S)-N-benzyl-5-thioxoproline tert-butyl ester (90741-31-4) → tert-butyl (2R,5R)-1-benzyl-5-(2-hydroxyethyl)pyrrolidine-2-carboxylate (90741-40-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.) Ph₃P, NMP / 1.) CH₃CN, 42 h, 2.) CH₂Cl₂, -5 deg C, 30 h.

2: 98 percent / H₂ / Pt/C / ethyl acetate / 16 h / 3102.9 Torr

3: 94 percent / LiBH₄ / diethyl ether / 4.5 h

With 1-methyl-pyrrolidin-2-one; lithium borohydride; hydrogen; triphenylphosphine; platinum on activated charcoal; In diethyl ether; ethyl acetate;

DOI:10.1021/jo960759m

Reference yield:

(2S)-1-benzyl-(E)-5-<(methoxycarbonyl)methylidene>proline tert-butyl ester (90741-33-6) → tert-butyl (2R,5R)-1-benzyl-5-(2-hydroxyethyl)pyrrolidine-2-carboxylate (90741-40-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / H₂ / Pt/C / ethyl acetate / 16 h / 3102.9 Torr

2: 94 percent / LiBH₄ / diethyl ether / 4.5 h

With lithium borohydride; hydrogen; platinum on activated charcoal; In diethyl ether; ethyl acetate;

DOI:10.1021/jo960759m

upstream raw materials:

(2R-cis)-5-((1,1-Dimethylethoxy)carbonyl)-1-(phenylmethyl)-2-pyrrolidineacetic acid methyl ester

(S)-N-benzyl-5-thioxoproline tert-butyl ester

(2S)-1-benzyl-(E)-5-<(methoxycarbonyl)methylidene>proline tert-butyl ester

(S)-tert-butyl 1-benzyl-5-oxopyrrolidine-2-carboxylate

Downstream raw materials:

(2S)-cis-1-(benzyloxycarbonyl)-5-vinylproline tert-butyl ester

(2S,5R)-5-(2-Bromo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

(2S,5R)-5-(2-Hydroxy-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

(2S,5R)-5-(2-Phenylselanyl-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester