(S)-(−)-4-Hydroxy-2-pyrrolidinone

Name: (<I>S</I>)-(−)-4-Hydroxy-2-pyrrolidinone
Brand: ALDRICH

97%

Synonym(s):

(S)-β-Hydroxy-γ-butyrolactam

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About This Item

Empirical Formula (Hill Notation):

C₄H₇NO₂

CAS Number:

68108-18-9

Molecular Weight:

101.10

UNSPSC Code:

12352005

NACRES:

NA.22

PubChem Substance ID:

24871604

MDL number:

MFCD00273370

Beilstein/REAXYS Number:

1524192

Assay:

97%

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Properties

Quality Level

100

assay

97%

optical activity

[α]23/D −43°, c = 1 in ethanol

mp

156-159 °C (lit.)

functional group

hydroxyl

SMILES string

O[C@@H]1CNC(=O)C1

InChI

1S/C4H7NO2/c6-3-1-4(7)5-2-3/h3,6H,1-2H2,(H,5,7)/t3-/m0/s1

InChI key

IOGISYQVOGVIEU-VKHMYHEASA-N

Description

General description

4-Hydroxy-2-pyrrolidinone is an important building block found in many bioactive compounds like streptopyrrolidine. It can be used as an intermediate in the synthesis of various γ-amino acids (GABA) and substituted 2-pyrrolidinones like cynometrine and cynodine.

Application

(S)-(−)-4-Hydroxy-2-pyrrolidinone can be used as a starting material in the preparation of:

Biologically significant pyrrolo[1,2:1′,2′]azepino[5,6-b]indole derivatives.
Substituted azepanes by reacting with various aldehydes via photochemical [5+2] cycloaddition.