Ammonium formate → Ammonia

Participants

Reaction Conditions

Reaction Steps

tert-butyl[2-(4-{[(3E)-4-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}but-3-en-1-yl]oxy}phenyl)ethyl]carbamate (Preparation 11, 725 mg, 1.05 mmol) was dissolved in ethanol (10 ml), palladium hydroxide (20% by weight on carbon, 181 mg, 0.25 mmol) then ammonium formate (529 mg, 8.39 mmol) was added and heated to 80° C. for 5 minutes then stirred at 75° C. for 1 hour. Reaction was cooled to room temperature and the mixture was filtered through Arbocel™ and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (97/3/0.3 to 94/6/0.6 by volume) to yield the title compound as a white foam, 460 mg.

Provenance & Evidence