N,N-Diethylethanamine trihydrofluoride → Ammonia

Participants

Reaction Steps

N-{2-(benzyloxy)-5-[(1R)-2-({2-[4-(2-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}ethoxy)phenyl]ethyl}amino)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (Preparation 22, 78 mg, 0.078 mmol) was dissolved in ethanol (2 ml), ammonium formate (200 mg, 3.17 mmol) was added, heated to reflux then palladium hydroxide (20% by weight on carbon, 50 mg, 0.07 mmol) was added and after 30 minutes the reaction was cooled to room temperature and the mixture was filtered through Arbocel™ and the solvent removed in vacuo. The residue was dissolved in tetrahydrofuran (2 ml) and N,N-diethylethanamine trihydrofluoride (59 μl, 0.37 mmol) was added and after 1 drop of methanol was added and the reaction mixture was stirred over night. The solvent was removed in vacuo and the residue dissolved in 1:1 methanol/880 ammonia, the solvents removed in vacuo and this process was repeated 4 times. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (230/20/2 to 90/10/1 by volume) to furnish the title compound as a white solid, 28 mg.

Provenance & Evidence