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Short Paper | Special issue | Vol 88, No. 2, 2014, pp.1649-1653
Published online, 20th November, 2013
DOI: 10.3987/COM-13-S(S)119
A Formal PCB-Free Synthesis of (-)-GSK1360707 via a Double Alkylation Reaction

Vassil I. Elitzin, Matthew J. Sharp, and Elie A. Tabet*

*Product Development, GlaxoSmithKline, Research Triangle Park, North Carolina 27709, U.S.A.

Abstract

The formal synthesis of the triple reuptake inhibitor (-)-GSK1360707 is described. The synthesis features an intramolecular cyclization and a double alkylation sequence to produce the 3-azabicyclo[4.1.0]heptane skeleton. An advantage of this route is the absence of PCB generation which plagued an earlier route.