Synthesis of (E)??N??[methyl??d3]??4??(3??pyridinyl)??3??buten??1??amine, a deuterated analogue of the nicotinic agonist RJR??2403

PA Crooks, A Ravard, GD Byrd

Index: Crooks, Peter A.; Ravard, Alain; Byrd, Gary D. Journal of Labelled Compounds and Radiopharmaceuticals, 1998 , vol. 41, # 12 p. 1165 - 1171

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Citation Number: 3

Abstract

Abstract The synthesis of (E)-N-[methyl-d 3]-4-(3-pyridinyl)-3-buten-1-amine ([methyl-d 3] RJR 2403;[methyl-d 3] metanicotine) is reported. The incorporation of deuterium was performed during the first step of the synthesis via N-methylation of the pyrrolidine nitrogen of racemic nornicotine with [methyl-d 3] iodomethane, in the presence of n-BuLi at− 70 C to afford racemic [methyl-d 3] nicotine in high yield (91%). The pyrrolidine ring was then ...