Potassium Iodide → Ammonia

Participants

Reaction Steps

(3R)-3-[5-{2-[3-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine (Preparation 38, 470 mg, 0.72 mmol), potassium iodide (120 mg, 0.72 mmol), sodium hydrogen carbonate (240 mg, 2.9 mmol) and {2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanol (Prepared according to WO2004/032921, 325 mg, 0.72 mmol) were stirred in propionitrile at 100° C. for 24 hours under nitrogen. After cooling to room temperature, water (100 ml) and ethyl acetate (100 ml) were added, organics separated and washed with brine (100 ml), dried (magnesium sulphate) and solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (100/0/0 to 8511511.5 by volume) to furnish the title compound as a brown glass, 450 mg.

Provenance & Evidence