A Short and Elegant Synthesis of (±)‐Streptopyrrolidine |
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| Authors: | Zurina Shaameri Sharifah Hidayah Sharif Ali Mohd Fazli Mohamat Bohari M Yamin Ahmad Sazali Hamzah |
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| Institution: | 1. Organic Synthesis Laboratory, Institute of Science,Universiti Teknologi MARA, , 40450 Shah Alam, Selangor, Malaysia;2. School of Chemical Sciences & Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, , 43600 Bangi, Selangor, Malaysia |
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| 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. |
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