An improved synthesis of 6-amino-1,2,3,4-tetrahydro-2-methylisoquinoline: elucidation of the stereochemistry of some diastereoisomers of 6-amino-2-methyldecahydroisoquinoline

Abstract

An improved synthesis of 6-amino-1,2,3,4-tetrahydro-2-methylisoquinoline is reported, along with the synthesis, isolation, and elucidation of the stereochemistry of three of the four possible diastereoisomers of the previously unreported 6-amino-2-methyldecahydroisoquinoline. Stereochemical assignments were made from a combination of chemical evidence, involving conversion of the amines into the corresponding known alcohols and oxidation of the alcohols to the corresponding ketones, and spectral data.