A practical and efficient synthesis of the selective neuronal acetylcholine-gated ion channel agonist (S)-(-)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl) pyridine maleate (SIB- …

…, A Herbaut, JS McCallum, IA McDonald

Index: Bleicher, Leo S.; Cosford, Nicholas D. P.; Herbaut, Audrey; Stuart McCallum; McDonald, Ian A. Journal of Organic Chemistry, 1998 , vol. 63, # 4 p. 1109 - 1118

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Citation Number: 98

Abstract

An efficient, high-yielding synthetic procedure for the preparation of the novel neuronal acetylcholine-gated ion channel agonist (S)-(-)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl) pyridine maleate [(S)-2, SIB-1508Y] is described. The key steps in the process include the lithium bis (trimethylsilyl) amide-mediated acylation of N-vinylpyrrolidinone with ethyl 5- bromonicotinate, a high-yielding sodium borohydride reduction of imine 5, and a new ...