2-But-3-enyl-5-oxo-pyrrolidine-1-carboxylic acid methyl ester

Base Information

• Chemical Name: 2-But-3-enyl-5-oxo-pyrrolidine-1-carboxylic acid methyl ester
• CAS No.: 108585-34-8
• Molecular Formula: C₁₀H₁₅NO₃
• Molecular Weight: 197.234
• Mol file: 108585-34-8.mol

Synonyms:2-But-3-enyl-5-oxo-pyrrolidine-1-carboxylic acid methyl ester

Chemical Property of 2-But-3-enyl-5-oxo-pyrrolidine-1-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 2-But-3-enyl-5-oxo-pyrrolidine-1-carboxylic acid methyl ester

There total 1 articles about 2-But-3-enyl-5-oxo-pyrrolidine-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:

methyl cyanoformate (17640-15-2) + (racemic)-5-(2'-butenyl)-2-pyrrolidinone (101347-86-8) → 2-But-3-enyl-5-oxo-pyrrolidine-1-carboxylic acid methyl ester (108585-34-8)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction; 1) THF, -78 deg C; 2) THF, -78 to 20 deg C;

DOI:10.1016/S0040-4039(00)85068-6

Reference yield:

2-But-3-enyl-5-oxo-pyrrolidine-1-carboxylic acid methyl ester (108585-34-8) → (+/-)-Anatoxin A (64285-06-9,85514-42-7,92142-32-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) NaBH₄; 2) H₂SO₄ / 1) EtOH, -20 deg C; 2) -20 to 20 deg C

2: 1) ozone; 2) dimethyl sulfide / 1) CH₂Cl₂, -78 deg C; 2) CH₂Cl₂, 48 h, 20 deg C

3: 83 percent / iPr₂NEt, LiCl / acetonitrile / 20 °C

4: 1) HCl; 2) DBN / 1) MeOH, -50 to 20 deg C, 18 h; 2) toluene, reflux

5: 55 percent / Me₃SiCl, NaI / acetonitrile / Heating

With hydrogenchloride; sodium tetrahydroborate; chloro-trimethyl-silane; dimethylsulfide; 2,6-dichloro-benzonitrile; sulfuric acid; ozone; N-ethyl-N,N-diisopropylamine; sodium iodide; lithium chloride; In acetonitrile;

DOI:10.1016/S0040-4039(00)85068-6

Reference yield:

ethanol (64-17-5) + 2-But-3-enyl-5-oxo-pyrrolidine-1-carboxylic acid methyl ester (108585-34-8) → 2-But-3-enyl-5-ethoxy-pyrrolidine-1-carboxylic acid methyl ester (108585-35-9)

Guidance literature:

With sodium tetrahydroborate; sulfuric acid; Yield given. Multistep reaction; 1) EtOH, -20 deg C; 2) -20 to 20 deg C;

DOI:10.1016/S0040-4039(00)85068-6

upstream raw materials:

methyl cyanoformate

(racemic)-5-(2'-butenyl)-2-pyrrolidinone

Downstream raw materials:

2-But-3-enyl-5-ethoxy-pyrrolidine-1-carboxylic acid methyl ester

(+/-)-Anatoxin A