Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 27, No. 7, 1988, pp.1685-1696
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4567
Introduction of Alkyl Groups at the α-Positions of Pyrrolidines and Piperidines: Synthesis of (±)-Coniine

Tatsuo Nagasaka,* Hideki Hayashim and Fumiko Hamaguchi

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


The conversion of lactams to α-alkylated cyclic amines is described. Reactions of α-ethoxyurethanes with trimethylsilyl cyanide in the presence of Levis acid afford the corresponding α-cyanourethanes, which, via carbanion, are alkylated to α-alkyl-α-cyanourethanes in moderate to high yields. Syntheses of (±)-coniine and trans-quinolizidine are carried out as model experiments for dealkoxycarbonylation and decyanation of 2-alkyl-1-alkoxycarbonyl-2-cyanopiperidines.