(S)-2-but-3-enyl-5-oxopyrrolidine-1-carboxylic acid methyl ester

Base Information

• Chemical Name: (S)-2-but-3-enyl-5-oxopyrrolidine-1-carboxylic acid methyl ester
• CAS No.: 861959-74-2
• Molecular Formula: C₁₀H₁₅NO₃
• Molecular Weight: 197.234
• Mol file: 861959-74-2.mol

Synonyms:(S)-2-but-3-enyl-5-oxopyrrolidine-1-carboxylic acid methyl ester

Chemical Property of (S)-2-but-3-enyl-5-oxopyrrolidine-1-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of (S)-2-but-3-enyl-5-oxopyrrolidine-1-carboxylic acid methyl ester

There total 3 articles about (S)-2-but-3-enyl-5-oxopyrrolidine-1-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: 91.0%

(R)-5-(but-3-en-1-yl)pyrrolidin-2-one (633294-91-4) + methyl chloroformate (79-22-1) → (S)-2-but-3-enyl-5-oxopyrrolidine-1-carboxylic acid methyl ester (861959-74-2)

Guidance literature:

(R)-5-(but-3-en-1-yl)pyrrolidin-2-one; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

methyl chloroformate; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 2.5h;

DOI:10.1021/jo0506682

Reference yield:

(S)-Pyroglutaminol (17342-08-4) → (S)-2-but-3-enyl-5-oxopyrrolidine-1-carboxylic acid methyl ester (861959-74-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 20 h / 20 °C

2.1: 51 percent / diethyl ether; tetrahydrofuran / 5 h / 20 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: 91 percent / tetrahydrofuran; hexane / 2.5 h / -78 - 0 °C

With dmap; n-butyllithium; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1021/jo0506682

Reference yield:

(S)-toluene-4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester (51693-17-5) → (S)-2-but-3-enyl-5-oxopyrrolidine-1-carboxylic acid methyl ester (861959-74-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 51 percent / diethyl ether; tetrahydrofuran / 5 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 91 percent / tetrahydrofuran; hexane / 2.5 h / -78 - 0 °C

With n-butyllithium; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1021/jo0506682

upstream raw materials:

(R)-5-(but-3-en-1-yl)pyrrolidin-2-one

methyl chloroformate

(S)-toluene-4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester

(S)-Pyroglutaminol

Downstream raw materials:

(+/-)-Anatoxin A