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Journal of Chemistry
Volume 2013, Article ID 475032, 6 pages
http://dx.doi.org/10.1155/2013/475032
Research Article

Enantioselective Synthesis of Antiepileptic Drug: (-)-Levetiracetam—Synthetic Applications of the Versatile New Chiral N-Sulfinimine

1Department of Research and Development, Inogent Laboratories Private Limited, 28A, IDA Nacharam, Hyderabad 500 076, India
2Centre for Pharmaceutical Sciences, Institute of Science and Technology, Jawaharlal Nehru Technological University, Kukatpally, Hyderabad 500 072, India
3R&D Centre, Orchid Chemicals & Pharmaceuticals Ltd., 476/14, Sholinganallur, Chennai 600 119, India

Received 11 January 2012; Accepted 3 May 2012

Academic Editor: Andreas G. Tzakos

Copyright © 2013 K. Chandra Babu et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

We report an asymmetric synthesis of (-)-Levetiracetam (1) in six steps starting from versatile new chiral N-sulfinimine (3). The key step, stereoselective 1,2-addition of ethylmagnesium bromide (EtMgBr) to chiral N-sulfinimine derived from (R)-glyceraldehyde acetonide and (S)-t-BSA, gave the corresponding sulfonamide (2) in high diastereoselectivity. Simultaneous deprotection and deacetylation followed by NaIO4 cleavage and reduction gave β-amino alcohol (6). Subsequent reactions yielded the targeted compound levetiracetam (1).