1-Benzyl-4-(ethoxycarbonyl)-1-azoniabicyclo[2.2.1]heptane bromide → Ethyl 1-azabicyclo[2.2.1]heptane-4-carboxylate hydrobromide

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Reaction Steps

A suspension of ethyl 1-benzyl-1-azoniabicyclo[2.2.1]hept-4-ylcarboxylate bromide (D16, 130 g, 0.38 mole) in ethanol (500 ml) was hydrogenated over 10% palladium on charcoal catalyst (8 g) at atmospheric temperature and pressure for 18 h. The catalyst was removed by filtering through celite, washing several times with hot ethanol, and the filtrate concentrated in vacuo to give the title compound (D17) as a crystalline white solid (80.1 g, 84%).

Provenance & Evidence