Potassium Iodide → Ammonia

Participants

Reaction Conditions

Reaction Steps

(3R)-3-[5-{2-[3-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine (Preparation 38, 340 mg, 0.52 mmol), potassium iodide (86 mg, 0.52 mmol), sodium hydrogen carbonate (175 mg, 2.08 mmol) and N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (Prepared according to WO2005/080324, 270 mg, 0.52 mmol) were added to propionitrile (5 ml) and stirred at 100° C. under nitrogen overnight. Mixture was cooled and water (100 ml) and ethyl acetate (100 ml) were added. Organics were separated and washed with brine (100 ml), 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 85/15/1.5 by volume) to furnish the title compound as a glass, 257 mg.

Provenance & Evidence