tert-Butyl 4-(3-aminophenyl)-5,6-dihydropyridine-1(2H)-carboxylate → tert-Butyl 4-(3-aminophenyl)piperidine-1-carboxylate

Participants

Reaction Steps

A mixture of 3.10 g of tert-butyl 4-(3-aminophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate (11.3 mmol) and 1.0 g of 10% Pd/C in 200 mL of ethanol was hydrogenated at room temperature using the balloon method for 2 days. The reaction mixture was filtered through Celite and washed with ethanol. The combined ethanol extracts were concentrated in vacuo and the residue was chromatographed on silica (dichloromethane:methanol:isopropylamine=95:5:1) to give 2.63 g of the desired product (84%): ESMS m/e: 277.2 (M+H)+.

Provenance & Evidence