Ammonium fluoride → HCID 57978278, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl(3-{2-[((2R)-2-[4-(benzyloxy)-3-(hydroxymethyl)phenyl]-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)amino]ethyl}phenyl)acetate (Preparation 54) (2.39 g, 4.14 mmol) in methanol (15 ml) and water (10 ml) was treated with ammonium fluoride (1.53 g, 41.4 mmol) and the reaction heated to 40° C. for 16 hours. The methanol was removed in vacuo and the aqueous residue extracted with dichloromethane (3×50 ml). The combined organics were dried (sodium sulfate) and the sovent removed in vacuo and the residue purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (97:3:0.3 changing to 95:5:0.5, by volume) to give the title compound as an orange gum (1.90 g).

Provenance & Evidence