Pivaloyl chloride → Ethyl 1-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]piperidin-4-carboxylate

Participants

Reaction Steps

Ethyl 1-(benzyloxycarbonylmethyl)isonipecotate was subjected to catalytic reduction under a hydrogen atmosphere of 1 atm in ethanol in the presence of 10% palladium-carbon. The resulting compound was treated with sodium methoxide in ethanol and then reacted with pivaloyl chloride in THF. The resulting compound was reacted with 3-(3-chlorobenzoyl)-2-ethylamino-6-methylpyridine under heating, and further treated with sodium methoxide in ethanol. Thereafter, the reaction mixture was worked up and purified in a usual manner to obtain ethyl 1-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]piperidin-4-carboxylate as a yellow oily substance. MS: 454.

Provenance & Evidence