N-Desmethyl Analogues of (+)-4-Dimethylamino-2,alpha-Dimethylphenethylamine. Synthesis and Configurational Relationships.

Abstract

The resolution of 4-dimethylamino-2,.alpha.-dimethylphenethylamine (1) [a monoamine oxidase inhibitor] and the synthesis of the 4-methylamino- and 4-amino-analogs 2 and 8 are described. The (+)2 was prepared from (+)1 by oxidative N-monodemethylation. The configurational relationships of (+)2 and (+)8 were established from the corresponding carbamates, which both on reduction yielded an identical compound, (+)-4-methylamino-2,.alpha.,N-trimethylphenethylamine dihydrochloride [(+)3]. In connection with the preparation of (+)3, the synthesis and selective ethoxycarbonylating properties of a new type of mixed anhydride agent are reported.