Synthesis of (±)??trans??2, 5??Dialkylpyrrolidines from the Lukes??Šorm Dilactam: Efficient Preparation of (±)??trans??2??Butyl??5??heptylpyrrolidine and Analogs Present in …

W Gessner, K Takahashi, A Brossi…

Index: Gessner; Takahashi; Brossi; Kowalski; Kaliner Helvetica Chimica Acta, 1987 , vol. 70, # 8 p. 2003 - 2010

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Citation Number: 23

Abstract

Abstract A 7-step synthesis of (±)-trans-2-butyl-5-heptylpyrrolidine (14) from the Lukes-Šorm dilactam 1 was accomplished in 6% overall yield without counting for a reconversion of cis- isomer 13 into trans-isomer 14 which was also accomplished. Reduction of pyrroline 12, the precursor of 14, with NaBH 4 afforded a 1: 1 mixture of cis-isomer 13 and trans-isomer 14 separated by chromatography. Reductive N-methylation of 14 afforded the N-methyl ...