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Synthesis 2001; 2001(3): 0364-0366
DOI: 10.1055/s-2001-11427
short paper
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Convenient Synthesis of 3,7-Diazabicyclo[3.3.1]nonane (Bispidine)

Yuji Miyahara* , Kenta Goto, Takahiko Inazu
  • *Department of Chemistry, Faculty of Science, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan; Fax + 81(92)6 42 26 07; E-mail: miyahscc@mbox.nc.kyushu-u.ac.jp
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Publication Date:
31 December 2001 (online)

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Bispidine 1a is conveniently synthesized via a route involving double Mannich reaction of 1-allylpiperidin-4-one to N,N′-diallylbispidinone, Wolff-Kishner reduction of the bispidinone, and deallylation of the resulting N,N′-diallylbispidine by treatment with ethyl chloroformate in the presence of NaI, followed by alkaline hydrolysis.

bicyclic compounds - Dieckman condensation - double Mannich reaction - deallylation

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