Tetrabutylammonium Fluoride → 8-(benzyloxy)-5-(1-(hydroxy)-2-(2-methyl-1-(3-(2-(1-adamantyl)ethoxy)phenyl)propan-2-ylamino)ethyl)quinolin-2(1H)-one

Participants

Reaction Steps

To a solution of Intermediate 88 (0.748 g, 1.02 mmol) in tetrahydrofuran (15 mL) were added 0.546 g (1.73 mmol) of tetrabutylammonium fluoride. The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the crude was partitioned between ethyl acetate and water. The organic layer was washed several times with water and the solvent was removed under reduced pressure. The crude was purified by column chromatography with silica gel, eluting with dichloromethane/methanol 90:4 to give 0.505 g (80% yield) of the title compound.

Provenance & Evidence