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

Base Information

• Chemical Name: (2S,5S)-2-Methyl-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester
• CAS No.: 185385-16-4
• Molecular Formula: C₁₅H₁₉NO₄S
• Molecular Weight: 309.386
• Mol file: 185385-16-4.mol

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

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

There total 2 articles about (2S,5S)-2-Methyl-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:

cis-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester (185385-14-2) + methyl iodide (74-88-4) → (2R,5R)-2-Methyl-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester (185385-17-5) + (2S,5S)-2-Methyl-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester (185385-16-4)

Guidance literature:

With lithium diisopropyl amide; Multistep reaction. Title compound not separated from byproducts; 1.) THF, 2.) THF, -78 deg C, 3 h;

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

Reference yield:

trans-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester (185385-15-3) + methyl iodide (74-88-4) → (2R,5R)-2-Methyl-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester (185385-17-5) + (2S,5S)-2-Methyl-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester (185385-16-4)

Guidance literature:

With lithium diisopropyl amide; Multistep reaction. Title compound not separated from byproducts; 1.) THF, 2.) THF, -78 deg C, 3 h;

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

Reference yield:

(2S,5S)-2-Methyl-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester (185385-16-4) → (S)-2-methylpyrrolidine-2-carboxylic acid (42856-71-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / Bu₃SnH / benzene / 1 h / 85 °C

2: 77 percent / Me₃SiI / CHCl₃ / 3 h / 60 °C

With trimethylsilyl iodide; tri-n-butyl-tin hydride; In chloroform; benzene;

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

upstream raw materials:

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

methyl iodide

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

Downstream raw materials:

(S)-2-methylpyrrolidine-2-carboxylic acid

(S)-2-Methyl-2-piperidinecarboxylic acid