☆ 4.6 Article

An improved synthesis of a selective serotonin reuptake inhibitor

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2008)

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ORGANIC PROCESS RESEARCH & DEVELOPMENT

卷 12, 期 2, 页码 178-182

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AMER CHEMICAL SOC

DOI: 10.1021/op700126w

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Chemistry, Applied Chemistry, Organic

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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 I in 8 chemical steps (5 isolations) in an overall yield of 38%.

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