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- Title
A Short and Elegant Synthesis of (±)-Streptopyrrolidine.
- Authors
Shaameri, Zurina; Ali, Sharifah Hidayah Sharif; Mohamat, Mohd Fazli; Yamin, Bohari M.; Hamzah, Ahmad Sazali
- Abstract
A brief and efficient approach for the synthesis of (±)-5-benzyl-4-hydroxy-2-pyrrolidine ( 1) from phenylalanine racemate is described. The key step is the stereocontrolled reduction of the keto functionality of benzylated pyrrolidinone intermediate ( 6) via sodium borohydride in carboxylic acid medium furnishing both ( R, R)- and ( S, S)-configured diastereomers. The natural ( R, R) enantiomer ( 2), however, crystallized out from its racemic mixture. Structure of 2 was confirmed by NMR, IR, elemental analyzer, and single crystal X-ray crystallographic techniques.
- Subjects
PYRROLIDINE synthesis; PHENYLALANINE; CHEMICAL reduction; SODIUM borohydride; BENZYL compounds; CARBOXYLIC acids; CRYSTAL structure
- Publication
Journal of Heterocyclic Chemistry, 2013, Vol 50, Issue 2, p320
- ISSN
0022-152X
- Publication type
Article
- DOI
10.1002/jhet.1078