Synthesis of Rimantadine from 1-Boraadamantane

Transformations of THF–1-boraadamantane 1 into 1-(1-hydroxyethyl)adamantane 5 and the hydrochioride salt of 1-(1-aminoethyl)adamantane (rimantadine) 9, based on a series of 1,2-anionotropic rearrangements in the corresponding ‘ate’-complexes, are presented.