Ammonium fluoride → HCID 11751411, compound

Participants

Reaction Conditions

Reaction Steps

Ammonium fluoride (98 mg, 2.64 mmol) was added in one portion to a stirred solution of 2-{3-[(2R)-2-({(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)propyl]phenyl}-N-cycloheptylacetamide (Preparation 1) (150 mg, 0.26 mmol) in methanol (3 ml) and water (1.5 ml) at room temperature. The reaction was heated at 40° C. for 18 hours and then allowed to cool to room temperature. The solvent was removed in vacuo and the residue dissolved in ethyl acetate (30 ml) and water (20 ml), the organic layer was separated, washed with brine (10 ml), dried (magnesium sulfate) and the solvent removed in vacuo to yield a clear oil. This was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol: ammonia (90:10:1 by volume) to furnish the title compound as a white foam (87 mg).

Provenance & Evidence