Aminobicyclo[2,2,1]heptanes. Part II. Diastereoisomeric dimethylaminobornyl acetates

Abstract

Methods of preparation of three diastereoisomeric aminobornanols [(VII)–(IX)] are described together with the attempted preparation of the fourth isomer. Observations on the direction of lithium aluminium hydride reductions used in these, and related reactions, are noted. Conversion of the aminobornanols into the title compounds [(XIII)–(XV)] is described. The n.m.r. spectral data of the final products and the intermediates are tabulated and various features of these spectra, such as long-range coupling [(X) and (XIII)] and splitting of the N-dimethyl signal [(XI), (X), (XV), and (XIX)], are discussed.