trans-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: trans-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester
• CAS No.: 185385-15-3
• Molecular Formula: C₁₄H₁₇NO₄S
• Molecular Weight: 295.359
• Mol file: 185385-15-3.mol

Synonyms:trans-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester

Chemical Property of trans-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of trans-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester

There total 3 articles about trans-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl 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:

(S)-dimethyl pyrrolidine-1,2-dicarboxylate (83541-81-5) + thiophenol (108-98-5) → cis-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester (185385-14-2) + trans-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester (185385-15-3)

Guidance literature:

(S)-dimethyl pyrrolidine-1,2-dicarboxylate; With lithium perchlorate; acetic acid; In nitromethane; at 0 ℃; Electrolysis;

thiophenol; In nitromethane; at 20 ℃; for 16h; Further stages.;

DOI:10.1021/ol026713z

Reference yield:

1-carbomethoxy-5-methoxy-L-proline methyl ester (185385-13-1) + thiophenol (108-98-5) → cis-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester (185385-14-2) + trans-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester (185385-15-3)

Guidance literature:

With boron trifluoride diethyl etherate; In diethyl ether; at -78 ℃; for 1.5h; Yield given. Yields of byproduct given;

DOI:10.1016/0040-4039(96)01919-3

Reference yield:

(S)-dimethyl pyrrolidine-1,2-dicarboxylate (83541-81-5) → trans-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester (185385-15-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / electrochemical oxidation

2: BF₃*Et₂O / diethyl ether / 1.5 h / -78 °C

With boron trifluoride diethyl etherate; In diethyl ether;

DOI:10.1016/0040-4039(96)01919-3

upstream raw materials:

1-carbomethoxy-5-methoxy-L-proline methyl ester

thiophenol

(S)-dimethyl pyrrolidine-1,2-dicarboxylate

Downstream raw materials:

(2R,5R)-2-Methyl-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester

(2S,5S)-2-Methyl-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester