Asymmetric Synthesis of a TRPV1 Antagonist via tert-Butanesulfinamide-Directed Reductive Amination with a Chromanone

…, SC Cullen, J Gandarilla, AW Kruger…

Index: Bellizzi, Mary E.; Bhatia, Ashok V.; Cullen, Steven C.; Gandarilla, Jorge; Kruger, Albert W.; Welch, Dennie S. Organic Process Research and Development, 2014 , vol. 18, # 2 p. 303 - 309

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Citation Number: 5

Abstract

An expedient asymmetric synthesis of TRPV1 antagonist 1 has been developed and demonstrated on multikilogram scale. The enabling route to 1 is detailed herein and characterized by the following key transformations: an aldol-cyclodehydration sequence to install the chromanone, and an auxiliary-mediated diastereoselective reductive amination.