Ammonium formate → Ammonia

Participants

Reaction Steps

8-(benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({9-[4-({3-[(R)-cyclohexyl(hydroxy)phenylmethyl]-1H-1,2,4-triazol-1-yl}methyl)piperidin-1-yl]nonyl}amino)ethyl]quinolin-2(1H)-one (Preparation 7, 230 mg, 0.255 mmol) was dissolved in ethanol (10 ml) and palladium hydroxide [20 wt. % (dry basis) on carbon (wet)] (5 mg) added followed by ammonium formate (161 mg, 2.55 mmol). After stirring at reflux for 1 hour the reaction mixture was filtered through Arbocelt® and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (97.5:2.5:0.25 to 90:10:1, by volume) to furnish the title compound as a glass, in 87% yield, 180 mg.

Provenance & Evidence