Ethanol → Ammonium Hydroxide

Participants

Reaction Steps

Catalytic hydrogenation of Cis(1,2,3,3a,9,9a-Hexahydro-cyclopenta[b]quinolin-4-yl)-acetonitrile (0.23 g, 1.08 mmol) in the presence of 5% Rh on Alumina and hydrogen (45 psi) in a 1:1 mixture of ethanol : ammonium hydroxide (40 ml) afforded the title compound. The reaction mixture was filtered through celite concentrated in vacuo and purified by flash chromatography (10% 2N NH3 in ethanol/dichloromethane) and converted to the HCl salt to give a white solid. The same step 4 procedure was used to prepare the trans isomer except that Trans (1,2,3,3a,9,9a-Hexahydro-cyclopenta[b]quinolin-4-yl)-acetonitrile was used instead of the cis isomer.

Provenance & Evidence