Experimental study demonstrates a streamlined synthesis of an SSRI candidate, highlighting improved yield and scalability through asymmetric cyclopropanation.
A practical synthesis of 3-((1 S, 2 S )-2-dimethylaminomethylcyclopropyl)-1 H -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%.
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Anthes et al. (2008) studied this question.
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