An Improved Synthesis of a Selective Serotonin Reuptake Inhibitor
Organic Process Research & Development2008Vol. 12(2), pp. 178–182
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Robert Anthes, Serge Benoit, Chien‐Kuang Chen, Elisabeth Corbett, Richard M. Corbett, Albert J. DelMonte, Stéphane Gingras, R. C. Livingston, Yadagiri Pendri, Justin B. Sausker, Maxime Soumeillant
Abstract
A practical synthesis of 3-((1S, 2S)-2-dimethylaminomethylcyclopropyl)-1H-indole-5-carbonitrile hydrochloride (1), a selective serotonin reuptake inhibitor (SSRI), is described. The process to prepare 1 was demonstrated on laboratory scale and highlights an enantioselective Simmons−Smith cyclopropanation of allylic alcohol 3 using Charette’s chiral dioxaborolane ligand. The improved synthesis enabled production of 1 in 8 chemical steps (5 isolations) in an overall yield of 38%.