The synthesis of OSU 6162: efficient, large-scale implementation of a Suzuki coupling

…, MT Maloney, MF Veley, DW VanderBor…

Index: Lipton, Michael F.; Mauragis, Michael A.; Maloney, Mark T.; Veley, Michael F.; VanderBor, Dale W.; Newby, John J.; Appell, Robert B.; Daugs, Edward D. Organic Process Research and Development, 2003 , vol. 7, # 3 p. 385 - 392

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Citation Number: 38

Abstract

The synthesis of the chiral, nonracemic 3-aryl piperidine, OSU 6162 (1), a potential CNS agent from Pharmacia Corporation, is presented. The key construction in the described synthesis is a palladium-catalyzed aryl cross-coupling reaction between bromosulfone (4) and pyridyl borane (14). Initially developed conditions for this Suzuki reaction, conducted in tetrahydrofuran/aqueous hydroxide, delivered free base (6) or hydrochloride salt (15a) in ...