Stereoselective Synthesis of (3R,5R)-cis-3-Hydroxy-5-phenylpyrrolidine

Kenji Maeda; Yuhei Yamamoto; Koji Tomimoto; Toshiaki Mase

doi:10.1055/s-2001-18106

Synlett 2001; 2001(11): 1808-1810
DOI: 10.1055/s-2001-18106

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Stereoselective Synthesis of (3R,5R)-cis-3-Hydroxy-5-phenylpyrrolidine

Kenji Maeda^* , Yuhei Yamamoto, Koji Tomimoto, Toshiaki Mase

^*Process Research, Process R&D, Laboratories for Technology Development, Banyu Pharmaceutical Co., Ltd, Kamimutsuna 3-chome-9-1, Okazaki, Aichi 444-0858, Japan; Fax + 81(564)51 70 86; E-mail: maedakj@banyu.co.jp

Abstract

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Cis-3-hydroxy-5-phenyl pyrrolidine could be synthesized stereoselectively from inexpensive starting materials, (R)-(+)-ethyl-4-chloro-3-hydroxybutanoate and (R)-(+)-4-chloro-3-hydroxybutyronitrile. Key feature involves face- and chemo-selective hydrogenation of cyclic imine 5 as the common key intermediate using Pt/C catalyst. Transformations described here will allow a practical synthesis of novel carbapenems, 1 and 2.

reductive amination - cyclic imine - hydrogenation - pyrrolidine - 1β-methylcarbapenem

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