Potassium Iodide → Ammonia

Participants

Reaction Conditions

Reaction Steps

7-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenoxy}heptan-1-amine bis hydrochloride salt (Preparation 18, 190 mg, 0.31 mmol), N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (Prepared according to WO2005/080324, 161 mg, 0.32 mmol), sodium hydrogen carbonate (106 mg, 1.26 mmol) and potassium iodide (52 mg, 0.32 mmol) were added to acetonitrile (5 ml) and heated to 90° C. for 24 hours, then left at room temperature over night, water and brine were added and extracted with ethyl acetate, 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 (98/2/0.2 to 92/8/0.8 by volume) to furnish the title compound as a colourless gum, 100 mg.

Provenance & Evidence