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Note | Regular issue | Vol 71, No. 5, 2007, pp.1127-1134
Published online, 9th March, 2007
DOI: 10.3987/COM-07-10994
Efficient Synthesis of (±)-N-Boc-pregabalin via Hetero-Diels-Alder Addition of Methyl 3-Nitrosoacrylate to Ethyl Vinyl Ether

John K. Gallos,* Elli S. Alexandraki, and Christos I. Stathakis

*Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece

Abstract

A new synthetic approach towards (±)-N-Boc-pregabalin is reported in this paper, which involves hetero-Diels-Alder addition of 3-nitrosoacrylate to ethyl vinyl ether and subsequent reduction of the C=N double bond of adduct, alteration of the ester functionality and reductive N-O bond scission followed by oxidation of the alcohol thus produced.