An Efficient Synthesis of Methyl 3-Carboxy-2-oxohexahydroazepine-1-acetate

Abstract

The title compound 1 is prepared from ε-caprolactam in a five-step sequence involving N-alkylation of the azepine ring from a 3-(phenylselanyl)-3-(benzyloxycarbonyl) derivative 4 and the generation of the 3-carboxyazepine moiety from the resulting diester 5 by ozonolysis followed by catalytic hydrogenation.

Keywords:

• Methyl 3-carboxy-2-oxohexahydroazepine-1-acetate
• ACE inhibitors
• NEP inhibitors, ε-Caprolactam

Acknowledgment

Thanks are due to the DURSI, Generalitat de Catalunya, for Grant 2001SGR-0084.