Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Synthesis of 1-Azabicyclo[3.3.0]octane Derivatives and Their Effects as Piracetam-like Nootropics
Mitsuru OKAYukiharu MATSUMOTOKiyotaka HIROOKATomoo SUZUKI
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2000 Volume 48 Issue 8 Pages 1121-1124

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Abstract

A useful pharmaceutical intermediate, 5-nitromethyl-1-azabicyclo[3.3.0]octane (1), was prepared in one step from 1, 7-dichloro-4-heptanone (4) under mild conditions. Catalytic hydrogenation of 1 over Raney Ni in the presence of sodium hydroxide afforded 5-aminomethyl-1-azabicyclo[3.3.0]octane (2) in high yield. Piracetam analogues 20-23, which were pyrrolidine derivatives involving a 1-azabicyclo[3.3.0]octane ring, were synthesized.Pharmacological tests showed that N-[(1-azabicyclo[3.3.0]octan-5-yl)methyl]-2-oxo-1-pyrrolidineacetamide (20) improves cerebral function.

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© The Pharmaceutical Society of Japan
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