The Synthesis of Optically Active N, N-Dimethy1-2-(methylphenyl-o-tolylsiloxy) ethanamine ( S i l a o r p h e nadrine)

Abstract

Synthesis of optically active silaorphenadrine, silicon analogue of orphenadrine [N, N-dimethyl2-[phenyl(o-tolyl)methoxy]ethanamine] was investigated. (Methylphenyl-o-tolylsilyl)methanamine, which wa s obtained by four steps reactions starting from dichlorodimethylsilane, was resolved by using 2-phenylpropionic acid as a resolving agent. The conversion of optically active (methylphenyl-o-tolylsilyl)methanamine to optically active methylphenyl-o-tolylsilane, a precursor for the synthesis of optically active sila456orphenadrine, was carried out successfully. Each of (+)-and (-)-isomer of silaorphenadrine was obtained by treating. (-)- and (+)-methylphenyl-o-tolylsilane with 2-(dimethylamino)ethanol in the presence of palladium/carbon, respectively. Configurations of silaorphenadrine and the intermediates were determined by the derivatization of methylphenyl-o-tolylsilane to methyl (1-naphthyl)phenylsilane system, of which configuration was already established.