Ammonium fluoride → Ammonia

Participants

Reaction Conditions

Reaction Steps

5-[(1R)-1-{[tert-buty(dimethyl)silyl]oxy}-2-({9-[4-({3-[(R)-cyclohexyl(hydroxy)phenylmethyl]-1H-1,2,4-triazol-1-yl}methyl)piperidin-1-yl]nonyl}amino)ethyl]-8-hydroxyquinolin-2(1H)-one (Preparation 8, 13.06 g, 16.06 mmol) was dissolved in methanol (430 ml) and ammonium fluoride (2.97 g, 80.3 mmol) was added. After stirring at 40° C. for 18 hours the solvent was removed in vacuo and the residue partitioned between dichloromethane/methanol (950 ml/50 ml) and saturated aqueous sodium bicarbonate solution (500 mL). The organic layer was separated and the aqueous layer further extracted with dichloromethane/methanol (450 ml/50 ml). The combined organic layers were dried over magnesium sulphate, filtered and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (90:10:1, by volume) to furnish the title compound as a yellow foam, in 72.3% yield, 8.12 g.

Provenance & Evidence