Ammonium formate → Ammonia

Participants

Reaction Steps

N-{2-(Benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-{[6-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)hexyl]amino}ethyl]phenyl}methanesulfonamide (Preparation 27, 530 mg, 0.55 mmol) was dissolved in ethanol and ammonium formate (700 mg, 10.9 mmol) and 10% palladium hydroxide on carbon (100 mg) was added. The reaction was heated under reflux for 12 hours, cooled to room temperature and further ammonium formate (600 mg, 9.37 mmol) and 10% palladium hydroxide on carbon (60 mg) added. The reaction was heated under reflux for 3 hours, cooled to room temperature and further 10% palladium hydroxide on carbon (60 mg) added. The reaction was heated under reflux for 3 hours, cooled to room temperature and filtered through Arbocel™. The filtrate solvent was removed in vacuo and the oil was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (80/20/2.0 by volume) to furnish the title compound as a yellow oil, 420 mg.

Provenance & Evidence