Stereoselective Synthesis of (R)‐3‐Methylthalidomide by Piperidin‐2‐one Ring Assembly Approach |
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Authors: | Shyam Raj Yadav Vinay Shankar Tiwari Wahajul Haq |
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Affiliation: | 1. Medicinal and Process Chemistry Division, CSIR‐Central Drug Research Institute, Lucknow, India;2. Academy of Scientific and Innovative Research, New Delhi, India |
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Abstract: | A simple and stereoselective synthesis of 3‐methylthalidomide, a configurationally stable thalidomide analog, is presented. Herein we describe the synthesis of (R)‐3‐methylthalidomide starting from (S)‐alanine by piperidin‐2‐one ring assembly approach in high yield and enantiomeric purity without using a chiral auxiliary or reagent. Starting from (R)‐alanine, the corresponding (S)‐3‐methylthalidomide can be prepared using the same methodology. Chirality 27:619–624, 2015. © 2015 Wiley Periodicals, Inc. |
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Keywords: | thalidomide teratogenic tumor necrosis factor‐α oxazolidinone enantioretentive alkylation |
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