(2R,3S)-1-[(R)-1-phenylethyl]-3-[(phenylsulfanyl)methyl]pyrrolidine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,3S)-1-[(R)-1-phenylethyl]-3-[(phenylsulfanyl)methyl]pyrrolidine-2-carboxylic acid methyl ester
• CAS No.: 506420-64-0
• Molecular Formula: C₂₁H₂₅NO₂S
• Molecular Weight: 355.501
• Mol file: 506420-64-0.mol

Synonyms:(2R,3S)-1-[(R)-1-phenylethyl]-3-[(phenylsulfanyl)methyl]pyrrolidine-2-carboxylic acid methyl ester

Chemical Property of (2R,3S)-1-[(R)-1-phenylethyl]-3-[(phenylsulfanyl)methyl]pyrrolidine-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-1-[(R)-1-phenylethyl]-3-[(phenylsulfanyl)methyl]pyrrolidine-2-carboxylic acid methyl ester

There total 2 articles about (2R,3S)-1-[(R)-1-phenylethyl]-3-[(phenylsulfanyl)methyl]pyrrolidine-2-carboxylic 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: 74.0%

S-Phenyl benzenethiosulfonate (1212-08-4) + (R)-[(but-3-enyl)(1-phenylethyl)amino]acetic acid methyl ester (186653-18-9) → (2R,3S)-1-[(R)-1-phenylethyl]-3-[(phenylsulfanyl)methyl]pyrrolidine-2-carboxylic acid methyl ester (506420-64-0)

Guidance literature:

(R)-[(but-3-enyl)(1-phenylethyl)amino]acetic acid methyl ester; With zinc dibromide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; for 4h;

S-Phenyl benzenethiosulfonate; With lithium chloride; In tetrahydrofuran; diethyl ether; at 0 - 20 ℃;

DOI:10.1021/jo026535n

Reference yield:

(R)-N-(but-3-en-1-yl)-N-(α-methylbenzyl)amine (177944-16-0) → (2R,3S)-1-[(R)-1-phenylethyl]-3-[(phenylsulfanyl)methyl]pyrrolidine-2-carboxylic acid methyl ester (506420-64-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 91.5 percent / K₂CO₃ / tetrahydrofuran; various solvent(s) / 0 - 20 °C

2.1: LDA; ZnBr₂ / tetrahydrofuran; diethyl ether / 4 h / -78 - 20 °C

2.2: 74 percent / CuCN; lithium chloride / tetrahydrofuran; diethyl ether / 0 - 20 °C

With potassium carbonate; zinc dibromide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jo026535n

Reference yield: 80.0%

(2R,3S)-1-[(R)-1-phenylethyl]-3-[(phenylsulfanyl)methyl]pyrrolidine-2-carboxylic acid methyl ester (506420-64-0) → (2R,3S)-1-[(R)-1-phenylethyl]-3-[(phenylsulfonyl)methyl]pyrrolidine-2-carboxylic acid methyl ester (506420-67-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/jo026535n

upstream raw materials:

S-Phenyl benzenethiosulfonate

(R)-[(but-3-enyl)(1-phenylethyl)amino]acetic acid methyl ester

(R)-N-(but-3-en-1-yl)-N-(α-methylbenzyl)amine

Downstream raw materials:

(2R,3S)-1-[(R)-1-phenylethyl]-3-[(phenylsulfonyl)methyl]pyrrolidine-2-carboxylic acid methyl ester

(2R,3S)-1-[(R)-1-phenylethyl]-3-[1-(phenylsulfonyl)ethyl]pyrrolidine-2-carboxylic acid methyl ester