(S)-4-Hydroxy-2-pyrrolidinone

Chemical Properties

White crystal

Uses

The (S)-enantiomer intermediate in the preparation of Oxiracetam

Uses

(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.

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.

Synthesis

10.1 g (100 mmol) of 2-oxiranylacetamide, CuI 0.95 g (5 mmol), cesium carbonate 2 g (200 mmol) was added to 150 ml of ammonia in a saturated solution of methanol, 55 for stirring reaction for 8 h, the reaction solution was concentrated under reduced pressure, 100 ml of water was added, dichloromethane extraction three times, saturated saline washed three times, the phase of ethyl acetate was concentrated under reduced pressure, and petroleum ether recrystallization to obtain (S)-(-)-4-hydroxy-2-pyrrolidinone 8.71g, yield 86.3%, HPLC purity 99.42% (area normalization method), ee value 99.67%.