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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 7
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Original Articles

A Synthesis of Captopril Through a Baylis–Hillman Reaction

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Pages 1141-1146 | Received 15 May 2002, Published online: 21 Aug 2006
 

Abstract

A synthesis of the antihipertensive amide 1, named captopril, is described. The strategy is based on a Baylis–Hillman reaction between N-acryloylproline and formaldehyde. Subsequential diastereoselective hydrogenation step and functional group interconversion provided captopril in good overall yield.

Acknowledgments

We wish to thank Prof. Dr. Fernando Coelho (IQ/UNICAMP) for ultrasound apparatus. The authors thank FAPESP for Melissa P. Feltrin's fellowship (99/10904-5).

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