1-Pyrrolidinecarboxylic acid, 2-(2S)-oxiranyl-, phenylmethyl ester, (2S)-

Base Information

• Chemical Name: 1-Pyrrolidinecarboxylic acid, 2-(2S)-oxiranyl-, phenylmethyl ester, (2S)-
• CAS No.: 881733-92-2
• Molecular Formula: C14H17NO3
• Molecular Weight: 247.294
• DSSTox Substance ID: DTXSID20469019
• Nikkaji Number: J2.650.057E
• Wikidata: Q82296580
• Mol file: 881733-92-2.mol

Synonyms:1-Pyrrolidinecarboxylic acid, 2-(2S)-oxiranyl-, phenylmethyl ester, (2S)-;881733-92-2;DTXSID20469019

Chemical Property of 1-Pyrrolidinecarboxylic acid, 2-(2S)-oxiranyl-, phenylmethyl ester, (2S)-

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 247.12084340
• Heavy Atom Count: 18
• Complexity: 301

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)OCC2=CC=CC=C2)C3CO3
• Isomeric SMILES: C1C[C@H](N(C1)C(=O)OCC2=CC=CC=C2)[C@H]3CO3

Technology Process of 1-Pyrrolidinecarboxylic acid, 2-(2S)-oxiranyl-, phenylmethyl ester, (2S)-

There total 2 articles about 1-Pyrrolidinecarboxylic acid, 2-(2S)-oxiranyl-, phenylmethyl ester, (2S)- 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: 27.0%

(2S)-(-)-phenylmethyl 2-vinylpyrrolidine-1-carboxylate (141521-11-1) → phenylmethyl (2S,2'R)-2-(oxiran-2-yl)pyrrolidine-1-carboxylate (905946-69-2) + phenylmethyl (2S,2'S)-2-(oxiran-2-yl)pyrrolidine-1-carboxylate (881733-92-2)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 20h;

DOI:10.1021/jm0510878

Reference yield:

C15H21NO6S → phenylmethyl (2S,2'S)-2-(oxiran-2-yl)pyrrolidine-1-carboxylate (881733-92-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; Reflux;

DOI:10.1016/j.tetlet.2008.09.095

Reference yield: 86.0%

phenylmethyl (2S,2'S)-2-(oxiran-2-yl)pyrrolidine-1-carboxylate (881733-92-2) + hexamethyldisilathiane (3385-94-2) → phenylmethyl (2S,1'S)-2-(1-hydroxy-2-mercaptoethyl)pyrrolidine-1-carboxylate (881734-00-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1055/s-2005-921922

upstream raw materials:

(2S)-(-)-phenylmethyl 2-vinylpyrrolidine-1-carboxylate

Downstream raw materials:

phenylmethyl (2S,1'S)-2-(1-hydroxy-2-mercaptoethyl)pyrrolidine-1-carboxylate