(S)-1-Benzyl-4-hydroxypyrrolidin-2-one

Base Information

• Chemical Name: (S)-1-Benzyl-4-hydroxypyrrolidin-2-one
• CAS No.: 191403-66-4
• Molecular Formula: C11H13 N O2
• Molecular Weight: 191.23
• European Community (EC) Number: 808-850-1
• DSSTox Substance ID: DTXSID40454245
• Nikkaji Number: J1.193.718G
• Wikidata: Q72441354
• Mol file: 191403-66-4.mol

Synonyms:191403-66-4;(S)-1-Benzyl-4-hydroxypyrrolidin-2-one;(S)-1-BENZYL-4-HYDROXY-2-PYRROLIDINONE;1-BENZYL-4(S)-HYDROXY-PYRROLIDIN-2-ONE;(4S)-1-Benzyl-4-hydroxypyrrolidin-2-one;SCHEMBL4922166;DTXSID40454245;OGAWUYQBXWYIJM-JTQLQIEISA-N;MFCD00672872;(S)-1-Benzyl-4-hydroxypyrrolidinone;AKOS006273116;(S)-N-benzyl-4-hydroxy-2-pyrrolidinone;AS-11583;(4S)-1-Benzyl-4-hydroxypyrrolidine-2-one;CS-0171335;A848389;(S)-1-benzyl-4-hydroxy-2-pyrrolidinone, AldrichCPR;2-Pyrrolidinone,4-hydroxy-1-(phenylmethyl)-,(4S)-;(S)-N-Benzyl-4-hydroxypyrrolidone;1-Benzyl-4(S)-hydroxy-pyrrolidin-2-one

Chemical Property of (S)-1-Benzyl-4-hydroxypyrrolidin-2-one

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 107.5-108℃
• Boiling Point: 405℃
• Flash Point: 199℃
• PSA: 40.54000
• Density: 1.261
• LogP: 0.71770
• Storage Temp.: 2-8°C
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 191.094628657
• Heavy Atom Count: 14
• Complexity: 211

Purity/Quality:

99% ^*data from raw suppliers

S-[N-Benzyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(CN(C1=O)CC2=CC=CC=C2)O
• Isomeric SMILES: C1[C@@H](CN(C1=O)CC2=CC=CC=C2)O
• Uses: (S)-1-Benzyl-4-hydroxy-2-pyrrolidinone can be biosynthesized using recombinant E. coli expressing P450pyr Monooxygenase.

Technology Process of (S)-1-Benzyl-4-hydroxypyrrolidin-2-one

There total 15 articles about (S)-1-Benzyl-4-hydroxypyrrolidin-2-one 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: 98.0%

(S)-N-benzyl-4-tert-butyldimethylsilyloxy-pyrrolidin-2-one (186428-91-1) → (S)-N-benzyl-4-hydroxy-pyrrolidin-2-one (191403-66-4)

Guidance literature:

(S)-N-benzyl-4-tert-butyldimethylsilyloxy-pyrrolidin-2-one; With hydrogenchloride; methanol; for 2h;

With sodium hydrogencarbonate; In methanol; at 0 ℃;

DOI:10.1021/jo901790g

Reference yield: 86.6%

methanol (67-56-1) + (4S,5R)-1-benzyl-4-hydroxy-5-thiophenol-2-pyrrolidinone (253608-06-9) → (S)-N-benzyl-4-hydroxy-pyrrolidin-2-one (191403-66-4)

Guidance literature:

(4S,5R)-1-benzyl-4-hydroxy-5-thiophenol-2-pyrrolidinone; With n-butyllithium; naphthalen-1-yl-lithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

methanol; In tetrahydrofuran; hexane; at -78 - 0 ℃;

DOI:10.1016/S0957-4166(99)00321-3

Reference yield: 70.0%

1-benzyl-2-pyrrolidone (5291-77-0) → (S)-N-benzyl-4-hydroxy-pyrrolidin-2-one (191403-66-4)

Guidance literature:

With Sphingomonas sp. HXN-200; for 5h;

DOI:10.1021/ol006735q

upstream raw materials:

methanol

(4S,5R)-1-benzyl-4-hydroxy-5-thiophenol-2-pyrrolidinone

methyl iodide

acetone

Downstream raw materials:

(S)-N-benzyl-3-hydroxypyrrolidine

(S)-1-benzyl-4-(a-diazoacetoxy)pyrrolidin-2-one

(4S)-4-hydroxypyrrolidin-2-one

Refernces

• 1、 -. "Gamma-lactam glycoside derivative, and synthesis method and application thereof". Paragraph 0017-0018. . Retrieved 2020/02/14.
• 2、 Sanyal, Ishita,Shukla, Brajesh,Barman, Piyali Deb,Banerjee, Asish Kumar. "Stereoselective synthesis of (S)-oxiracetam and (S)-GABOB from (R)-glyceraldehyde acetonide". supporting information. p. 2637 - 2640. Retrieved 2013/06/26.