A Short and Elegant Synthesis of (±)-Streptopyrrolidine
Zurina Shaameri
Organic Synthesis Laboratory, Institute of Science,Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia
Search for more papers by this authorSharifah Hidayah Sharif Ali
Organic Synthesis Laboratory, Institute of Science,Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia
Search for more papers by this authorMohd Fazli Mohamat
Organic Synthesis Laboratory, Institute of Science,Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia
Search for more papers by this authorBohari M. Yamin
School of Chemical Sciences & Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia
Search for more papers by this authorCorresponding Author
Ahmad Sazali Hamzah
Organic Synthesis Laboratory, Institute of Science,Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia
E-mail: [email protected]Search for more papers by this authorZurina Shaameri
Organic Synthesis Laboratory, Institute of Science,Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia
Search for more papers by this authorSharifah Hidayah Sharif Ali
Organic Synthesis Laboratory, Institute of Science,Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia
Search for more papers by this authorMohd Fazli Mohamat
Organic Synthesis Laboratory, Institute of Science,Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia
Search for more papers by this authorBohari M. Yamin
School of Chemical Sciences & Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia
Search for more papers by this authorCorresponding Author
Ahmad Sazali Hamzah
Organic Synthesis Laboratory, Institute of Science,Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia
E-mail: [email protected]Search for more papers by this authorAbstract
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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