Water → Ammonia

Participants

Reaction Conditions

Reaction Steps

4-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(2-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}ethoxy)phenyl]ethyl}amino)ethyl]-2-(hydroxymethyl)phenol (Preparation 49, 235 mg, 0.30 mmol) was dissolved in methanol (2.9 ml) and water (1.4 ml) and ammonium fluoride (112 mg, 3.0 mmol) was added. The reaction was heated to 40° C. and stirred overnight, cooled to room temperature and then saturated aqueous sodium hydrogen carbonate (20 ml) and ethyl acetate (20 ml) were added. The aqueous was separated and extracted with ethyl acetate and the combined organics dried (magnesium sulphate) and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (80/20/1.0 by volume) to furnish the title compound as a glass, 55 mg.

Provenance & Evidence