Studies on Structure-Activity Relationship of Analgetics. X. Syntheses of 11-Amino-2, 3-benzobicyclo [3. 3. 1] nonane and 3-Phenyl-9-amino-bicyclo [3. 3. 1] nonane Derivatives.

Abstract

Some derivatives of 11-amino-2, 3-benzobicyclo [3. 3. 1] nonane and 3-phenyl-9-amino-bicyclo [3. 3. 1] nonane were synthesized from β-tetralon and 4-phenylcyclohexanone, respectively, through an enamine cyclization. Configuration and conformation of these bicyclic compounds were elucidated by nuclear magnetic resonance spectral analysis. A peculiar property, resembling to Sommelet reaction, of the amino group attached to bridged methylene in bicyclic system is presented. The mass spectra of the amino derivatives of bicyclo [3. 3. 1] nonane system are discussed.