(2S)-5-oxo-1-[(3-phenylmethoxyphenyl)methyl]pyrrolidine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S)-5-oxo-1-[(3-phenylmethoxyphenyl)methyl]pyrrolidine-2-carboxylic acid methyl ester
• CAS No.: 1308718-80-0
• Molecular Formula: C₂₀H₂₁NO₄
• Molecular Weight: 339.391

Synonyms:(2S)-5-oxo-1-[(3-phenylmethoxyphenyl)methyl]pyrrolidine-2-carboxylic acid methyl ester

Chemical Property of (2S)-5-oxo-1-[(3-phenylmethoxyphenyl)methyl]pyrrolidine-2-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (2S)-5-oxo-1-[(3-phenylmethoxyphenyl)methyl]pyrrolidine-2-carboxylic acid methyl ester

There total 3 articles about (2S)-5-oxo-1-[(3-phenylmethoxyphenyl)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: 65.0%

3-benzyloxybenzyl bromide (1700-31-8) + methyl (S)-pyroglutamate (4931-66-2) → (2S)-5-oxo-1-[(3-phenylmethoxyphenyl)methyl]pyrrolidine-2-carboxylic acid methyl ester (1308718-80-0)

Guidance literature:

With sodium hydride; In tetrahydrofuran; paraffin oil; at 0 - 20 ℃;

DOI:10.1016/j.bmc.2011.03.044

Reference yield:

(3-(benzyloxy)phenyl)methanol (1700-30-7) → (2S)-5-oxo-1-[(3-phenylmethoxyphenyl)methyl]pyrrolidine-2-carboxylic acid methyl ester (1308718-80-0)

Guidance literature:

Multi-step reaction with 2 steps

1: phosphorus tribromide / diethyl ether / 3 h / 20 °C / Cooling with ice

2: sodium hydride / tetrahydrofuran; paraffin oil / 0 - 20 °C

With phosphorus tribromide; sodium hydride; In tetrahydrofuran; diethyl ether; paraffin oil;

DOI:10.1016/j.bmc.2011.03.044

Reference yield:

L-Pyroglutamic acid (98-79-3) → (2S)-5-oxo-1-[(3-phenylmethoxyphenyl)methyl]pyrrolidine-2-carboxylic acid methyl ester (1308718-80-0)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride

2: sodium hydride / tetrahydrofuran; paraffin oil / 0 - 20 °C

With thionyl chloride; sodium hydride; In tetrahydrofuran; paraffin oil;

DOI:10.1016/j.bmc.2011.03.044

upstream raw materials:

3-benzyloxybenzyl bromide

methyl (S)-pyroglutamate

(3-(benzyloxy)phenyl)methanol

L-Pyroglutamic acid

Downstream raw materials:

4-methylbenzenesulfonic acid [5-oxo-1-[[3-(phenylmethoxy)phenyl]methyl]-(2S)-pyrrolidinyl]methyl ester

(5S)-(hydroxymethyl)-1-[[3-(phenylmethoxy)phenyl]methyl]-2-pyrrolidinone

1-[(3-hydroxyphenyl)methyl]-(5S)-(1H-imidazol-1-ylmethyl)-2-pyrrolidinone

(5S)-(1H-imidazol-1-ylmethyl)-1-[[3-(phenylmethoxy)phenyl]methyl]-2-pyrrolidinone

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