Benzylamine, 2,3-dimethoxy methyl

Die optisch-aktiven a-Methyl-benzylamine cyclisieren mit erythro- oder t/izeo-2,3-Dibrom-butansaure-estern zu den entsprechenden chiralen (1R)- bzw. (75)-2,3-/ra s-Dimethoxy-carbonyl-l-(l-phenyl-ethylamino)-aziridinen. Sie werden katalytisch zu (S)- bzw. (R)-As-paraginsaure hydriert und verseift13. 

Benzyl alcohol, o-methyl-, 34, 58 Benzylamine, 35, 91 Benzylamine, 2,3-dimethoxy-N-methyl, 30, 59 N,N,o-trimethyl-, 34, 61... 

The optical isomers of DOM have been prepared in two ways. The racemic base has been resolved as the ortho-nitrotartranilic acid salt by recrystallization from EtOH. The (+) acid provides the (+) or S isomer of DOM preferentially. Also, the above-mentioned l-(2,5-dimethoxy-4-methylphenyl)-2-propanone can be reductively aminated with optically active alpha-methyl benzylamine with Raney Nickel. This amine is isolated and purified by recrystallization of the hydrochloride salt. When optically pure, the benzyl group was removed by hydrogenolysis with palladium on carbon. The mp of either of the optical isomers, as the hydrochloride salts, was 204-205 °C. 

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