Potassium Iodide → Ammonia

Participants

Reaction Conditions

Reaction Steps

tert-butyl[2-(3-hydroxyphenyl)ethyl]carbamate (Preparation 35, 1.7 g, 5.96 mmol), potassium carbonate (1.65 g, 11.9 mmol), potassium iodide (5.0 g, 0.03 mmol) and 2-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl)ethyl methanesulfonate (Preparation 36, 1.56 g, 2.98 mmol) were stirred in dimethylformamide (20 ml) and stirred at 60° C. overnight. After cooling, water (250 ml) and diethyl ether (250 ml) were added, organics separated and washed with water (100 ml×3), brine (150 ml) then 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 (100/0/0 to 90/10/1.0 by volume) to furnish the title compound as an oil, 1.3 g.

Provenance & Evidence