Process for the preparation of 2,3-cis-1,2,3,4- tetrahydro-5-(2-hydroxy-3-tert.butylamino) propoxy-2,3-naphthalenediol

Abstract From the Canadian patent

A new process is provided herein for the preparation of the therapeutically-useful product 2,3-cis-1,2,3,4-tetrahydro-5-(2hydroxy)-5-tert,butylamino)propoxyl-2,3-naphthalenediol a, compound having Formula (I), (I), 5,8-Dihydro-1-naphthol-1-acetate is first oxidized with Nmethylmorpholine-N-oxide and a catalytic amount of osmium tetroxide to form cis-2,3-dihydroxy-1,2,3,4-tetrahydronaphthalene-5-acetate, which is then converted with acetone to the corresponding acetonide having the Formula (V). That acetonide is reacted by a phase-transfer technique in a sodium hydroxide solution - dichloromethane mixture in the presence of a quarternary alkyl ammonium halide with epichlorohydrin to form a …