Synthesis of optically active 2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (nicardipine).

Abstract
(+)- and (-)-2-(N-benzyl-N-methylamino)ethylmethyl-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (6) (nicardipine) were synthesized from (-)- and (+)-1-ethoxymethyl-5-methoxycarbonyl-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (3), respectively. Resolution of 3 was carried out using cinchonidine and cinchonine as resolving agents. The vertebral vasodilating activity of (+)-YC-93 [2-(N-benzyl-N-methylamino)ethylmethyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride] was .apprx. 3 times that of (-)-YC-93 in dogs.

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