(S)-1-Benzyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester

Base Information

• Chemical Name: (S)-1-Benzyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester
• CAS No.: 428518-44-9
• Molecular Formula: C13H15 N O3
• Molecular Weight: 233.2631
• Hs Code.: 2933790090
• DSSTox Substance ID: DTXSID40350778
• Nikkaji Number: J1.723.247I
• Wikidata: Q82126882
• Mol file: 428518-44-9.mol

Synonyms:428518-44-9;(S)-1-Benzyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester;(S)-Methyl 1-benzyl-5-oxopyrrolidine-3-carboxylate;methyl (3S)-1-benzyl-5-oxopyrrolidine-3-carboxylate;(s)-1-benzyl-5-oxo-pyrrolidine-3-carboxylic acidmethyl ester;SCHEMBL5970008;DTXSID40350778;MFCD09261309;AKOS022172417;AS-36256;CS-0172487;A826032;(S)-Methyl1-benzyl-5-oxopyrrolidine-3-carboxylate;Methyl(S)-1-benzyl-5-oxopyrrolidine-3-carboxylate;1-Benzyl-5-oxopyrrolidine-3beta-carboxylic acid methyl ester;(3S)-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxylic acid methyl ester;methyl (3S)-5-oxidanylidene-1-(phenylmethyl)pyrrolidine-3-carboxylate

Chemical Property of (S)-1-Benzyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester

Chemical Property:

• Boiling Point: 396.6°Cat760mmHg
• PKA: -1.82±0.40(Predicted)
• Flash Point: 193.6°C
• PSA: 46.61000
• Density: 1.213g/cm³
• LogP: 1.14600
• Storage Temp.: 2-8°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 233.10519334
• Heavy Atom Count: 17
• Complexity: 297

Purity/Quality:

98%min ^*data from raw suppliers

(S)-Methyl1-benzyl-5-oxopyrrolidine-3-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1CC(=O)N(C1)CC2=CC=CC=C2
• Isomeric SMILES: COC(=O)[C@H]1CC(=O)N(C1)CC2=CC=CC=C2

Technology Process of (S)-1-Benzyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester

There total 8 articles about (S)-1-Benzyl-5-oxo-pyrrolidine-3-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: 82.0%

methanol (67-56-1) + (S)-(+)-1-(phenylmethyl)-5-oxo-3-pyrrolidinecarboxylic acid (428518-42-7) → methyl (S)-1-(phenylmethyl)-5-oxo-3-pyrrolidinecarboxylate (428518-44-9)

Guidance literature:

With acetic acid; diazomethyl-trimethyl-silane; In toluene; at 20 ℃; for 18h; Schlenk technique;

DOI:10.1021/acs.orglett.6b02074

Reference yield: 28.0%

methyl 1-benzyl-5-oxo-3-pyrrolidinecarboxylate (51535-00-3) → (S)-(+)-1-(phenylmethyl)-5-oxo-3-pyrrolidinecarboxylic acid (428518-42-7) + methyl (R)-(-)-1-(phenylmethyl)-5-oxo-3-pyrrolidinecarboxylate (428518-36-9) + methyl (S)-1-(phenylmethyl)-5-oxo-3-pyrrolidinecarboxylate (428518-44-9)

Guidance literature:

With α-chymotrypsine (α-CT); In phosphate buffer; at 20 ℃; pH=7.4; low conversion;

DOI:10.1016/S0957-4166(01)00523-7

Reference yield:

ethyl 1-benzyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate → methyl (S)-1-(phenylmethyl)-5-oxo-3-pyrrolidinecarboxylate (428518-44-9)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium trimethylsilonate / toluene / 4 h / 60 °C

2: ((S)-1-{(Sp)-2-[2-(dicyclohexylphosphino)phenyl]ferrocenyl}ethylbis[3,5-bis(trifluoromethyl)phenyl]phosphine); bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen / methanol / 18 h / 22502.3 Torr / Sealed tube; Inert atmosphere

3: diazomethyl-trimethyl-silane; acetic acid / toluene / 18 h / 20 °C / Schlenk technique

With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; ((S)-1-{(Sp)-2-[2-(dicyclohexylphosphino)phenyl]ferrocenyl}ethylbis[3,5-bis(trifluoromethyl)phenyl]phosphine); potassium trimethylsilonate; hydrogen; acetic acid; diazomethyl-trimethyl-silane; In methanol; toluene;

DOI:10.1021/acs.orglett.6b02074

upstream raw materials:

diazomethane

(S)-(+)-1-(phenylmethyl)-5-oxo-3-pyrrolidinecarboxylic acid

methyl 1-benzyl-5-oxo-3-pyrrolidinecarboxylate

Dimethyl itakonate

Downstream raw materials:

(3S)-pyrrolidine-3-carboxylic acid methyl ester

methyl (S)-(+)-1-(phenylmethyl)-3-pyrrolidinecarboxylate

Refernces

• 1、 Felluga, Fulvia,Pitacco, Giuliana,Prodan, Massimo,Pricl, Sabrina,Visintin, Marco,Valentin, Ennio. "A chemoenzymatic approach to the synthesis of enantiomerically pure aza analogues of paraconic acid methyl ester and both enantiomers of methyl β-proline". . p. 3241 - 3249. Retrieved 2007/10/03.