Synthesis of 1, 2, 3, 4, 5, 6-Hexahydro-1, 5-methano-2-methylpyrido [2, 3-c] azocine

Abstract

Synthesis of benzomorphan analog of which aromatic ring is heterocyclic was investigated. The key compounds of this synthetic route, 2-benzoyl-2-azabicyclo [3.3.1]-nonan-8-one derivatives (X, and XII), were prepared starting from ethyl 4-pyridinepropionate (I). 1, 2, 3, 4, 5, 6-Hexahydro-1, 5-methanopyrido [2, 3-c] azocine derivative (XV) was synthesized by condensation of XII with 3-aminoacrolein. Furthermore, the pyrazolone derivative (XI) was also prepared from X by treatment with hydrazine, and the pyrimidine derivative (XIV) was obtained from XII via the β-diketone (XIII).