N,N-Diethylethanamine trihydrofluoride → Ammonia

Participants

Reaction Steps

5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(2-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}ethoxy)phenyl]ethyl}amino)ethyl]benzene-1,3-diol (Preparation 44, 174 mg, 0.23 mmol) was dissolved in methanol (5 ml) and tetrahydrofuran (10 ml), and triethylaminetrihydrofluoride (0.23 ml, 1.4 mmol) added. The mixture was stirred overnight and then the solvent removed in vacuo. The residue was dissolved in methanol (10 ml) and 880 ammonia (1 ml) and the solvent removed under reduced pressure. This was repeated and the residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (95/5/0.5 to 80/20/2.0 by volume) to furnish the title compound as a foam, 83 mg.

Provenance & Evidence