Synthesis and nuclear magnetic resonance spectra of substituted aminobornanes

Abstract

The synthesis of the epimers of 2-acetoxy-3-endo-dimethylaminobornane and of 3-acetoxy-2-endo-dimethylaminobornane through the intermediacy of the corresponding dimethylaminobornanols is described. Quaternisation of the acetates afforded analogues of acetylcholine in which the ‘onium’ and acetoxy-systems are held in a rigid cis and trans relationship. The n.m.r. spectral data of these quaternary salts and of all intermediates are presented. Chemical shift values are assigned to the three methyl groups of the bornane skeleton and the influence of spatially proximate electronegative functions on these absorptions and on those of the 2- and 3-protons is discussed.