(2s)-2-(2-Oxopyrrolidin-1-yl)butanoic acid methyl ester

Base Information

• Chemical Name: (2s)-2-(2-Oxopyrrolidin-1-yl)butanoic acid methyl ester
• CAS No.: 358629-51-3
• Molecular Formula: C₉H₁₅NO₃
• Molecular Weight: 185.223
• European Community (EC) Number: 642-913-2
• UNII: EP346LRF5C
• DSSTox Substance ID: DTXSID501335340
• Nikkaji Number: J2.360.849I
• Mol file: 358629-51-3.mol

Synonyms:UNII-EP346LRF5C;Levetiracetam methyl ester;358629-51-3;EP346LRF5C;(2s)-2-(2-oxopyrrolidin-1-yl)butanoic acid methyl ester;(S)-2-(2-Oxopyrrolizino)butanoic acid methyl ester;1-Pyrrolidineacetic acid, alpha-ethyl-2-oxo-, methyl ester, (alphaS)-;SCHEMBL1880935;QRQVFVYABBZXFO-ZETCQYMHSA-N;DTXSID501335340;AKOS015917970;S-PYRROLIDINYL BUTYNIL METHYL ESTER;(S)-alpha-ethyl-2-oxo pyrrolidine acetic acid methyl ester;1-PYRROLIDINEACETIC ACID, .ALPHA.-ETHYL-2-OXO-, METHYL ESTER, (.ALPHA.S)-

Chemical Property of (2s)-2-(2-Oxopyrrolidin-1-yl)butanoic acid methyl ester

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Boiling Point: 309.0±25.0 °C(Predicted)
• PKA: -0.78±0.20(Predicted)
• Density: 1.123±0.06 g/cm3(Predicted)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 185.10519334
• Heavy Atom Count: 13
• Complexity: 215

Purity/Quality:

99%+, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C(=O)OC)N1CCCC1=O
• Isomeric SMILES: CC[C@@H](C(=O)OC)N1CCCC1=O

Technology Process of (2s)-2-(2-Oxopyrrolidin-1-yl)butanoic acid methyl ester

There total 12 articles about (2s)-2-(2-Oxopyrrolidin-1-yl)butanoic 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: 100.0%

methanol (67-56-1) → (S)-methyl 2-(2-oxopyrrolidin-1-yl)-2-butanoate (358629-51-3) + (R)-1-phenyl-ethyl-amine (3886-69-9)

Guidance literature:

(-)-(S)-alpha-ethyl-2-oxo-1-pyrrolidineacet-N-(+)-(R)-(1-phenylethyl)-amide; With sulfonic acid type-ion exchange resin; water; In toluene; for 6h; not specified Heating / reflux;

methanol; With sulfonic acid type-ion exchange resin; In water; toluene; at 60 ℃; for 3h;

Reference yield: 95.0%

methyl (2S)-2-(3,4-dichloro-2,5-dihydro-2-oxo-1H-pyrrol-1-yl)butanoate → (S)-methyl 2-(2-oxopyrrolidin-1-yl)-2-butanoate (358629-51-3)

Guidance literature:

With hydrogen; triethylamine; palladium on activated charcoal; In ethanol; for 2h; under 2587.71 Torr;

DOI:10.1002/ejoc.200600153

Reference yield: 87.5%

methanol (67-56-1) → (S)-methyl 2-(2-oxopyrrolidin-1-yl)-2-butanoate (358629-51-3)

Guidance literature:

(-)-(S)-alpha-ethyl-2-oxo-1-pyrrolidineacet-N-(+)-(R)-(1-phenylethyl)-amide; With ethyl-thiophenyl-sulfonic acid supported on silica; In toluene; for 5h; silica Heating / reflux;

methanol; With ethyl-thiophenyl-sulfonic acid supported on silica; In toluene; at 60 ℃; for 3h; Product distribution / selectivity;

upstream raw materials:

methanol

(2S)-2-(2-oxopyrrolidin-1-yl)butanoic acid

(S)-methyl-4-(1-methoxycarbonylpropylamino)butyrate

ethyl-(S)-4-[(1-methoxycarbonyl)propylamino]butyrate

Downstream raw materials:

levetiracetam

Refernces

• 1、 -. "Process for the preparation of Levetiracetam". Page/Page column 4. . Retrieved 2011/04/18.
• 2、 Khiri, Naima,Bertrand, Etienne,Ondel-Eymin, Marie-Joelle,Rousselin, Yoann,Bayardon, Jerome,Harvey, Pierre D.,Juge, Sylvain. "Enantioselective hydrogenation catalysis aided by a σ-bonded calix[4]arene to a p-chirogenic aminophosphane phosphinite rhodium complex". scheme or table. p. 3622 - 3631. Retrieved 2010/10/04.