A short and elegant synthesis of (±)-streptopyrrolidine

Zurina Shaameri, Sharifah Hidayah Sharif Ali, Mohd Fazli Mohamat, Bohari Mohd. Yamin, Ahmad Sazali Hamzah

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

A brief and efficient approach for the synthesis of (±)-5-benzyl-4- hydroxy-2-pyrrolidine () from phenylalanine racemate is described. The key step is the stereocontrolled reduction of the keto functionality of benzylated pyrrolidinone intermediate () via sodium borohydride in carboxylic acid medium furnishing both (R,R)- and (S,S)-configured diastereomers. The natural (R,R) enantiomer (), however, crystallized out from its racemic mixture. Structure of was confirmed by NMR, IR, elemental analyzer, and single crystal X-ray crystallographic techniques.

Original languageEnglish
Pages (from-to)320-325
Number of pages6
JournalJournal of Heterocyclic Chemistry
Volume50
Issue number2
DOIs
Publication statusPublished - Mar 2013

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Pyrrolidinones
Enantiomers
Carboxylic Acids
Phenylalanine
Nuclear magnetic resonance
Single crystals
X rays
sodium borohydride
pyrrolidine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Shaameri, Z., Ali, S. H. S., Mohamat, M. F., Mohd. Yamin, B., & Hamzah, A. S. (2013). A short and elegant synthesis of (±)-streptopyrrolidine. Journal of Heterocyclic Chemistry, 50(2), 320-325. https://doi.org/10.1002/jhet.1078

A short and elegant synthesis of (±)-streptopyrrolidine. / Shaameri, Zurina; Ali, Sharifah Hidayah Sharif; Mohamat, Mohd Fazli; Mohd. Yamin, Bohari; Hamzah, Ahmad Sazali.

In: Journal of Heterocyclic Chemistry, Vol. 50, No. 2, 03.2013, p. 320-325.

Research output: Contribution to journalArticle

Shaameri, Z, Ali, SHS, Mohamat, MF, Mohd. Yamin, B & Hamzah, AS 2013, 'A short and elegant synthesis of (±)-streptopyrrolidine', Journal of Heterocyclic Chemistry, vol. 50, no. 2, pp. 320-325. https://doi.org/10.1002/jhet.1078
Shaameri Z, Ali SHS, Mohamat MF, Mohd. Yamin B, Hamzah AS. A short and elegant synthesis of (±)-streptopyrrolidine. Journal of Heterocyclic Chemistry. 2013 Mar;50(2):320-325. https://doi.org/10.1002/jhet.1078
Shaameri, Zurina ; Ali, Sharifah Hidayah Sharif ; Mohamat, Mohd Fazli ; Mohd. Yamin, Bohari ; Hamzah, Ahmad Sazali. / A short and elegant synthesis of (±)-streptopyrrolidine. In: Journal of Heterocyclic Chemistry. 2013 ; Vol. 50, No. 2. pp. 320-325.
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