Tetrabutylammonium Fluoride → HCID 11754517, compound

Participants

Reaction Steps

To a stirred solution of 2-(trimethylsilyl)ethyl 4-{4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)oxy]phenyl}butanoate (42 mg, 0.07 mmol) in THF at rt was added, drop-wise, TBAF (70 μL of a 1.0M solution in THF, 0.07 mmol) and the mixture stirred at rt for 1.5 hours. Additional TBAF (35 μL of a 1.0M solution in THF, 0.04 mmol) was then added and the mixture left to stir at rt for 17.5 hours. The mixture was then concentrated under vacuum and the residue purified by SPE (silica, 1 g Cartridge) eluting with cyclohexane:EtOAc (gradient 25:1 to 0:1), then EtOAc:MeOH (gradient 10:1 to 0:1) to give a crude product which was purified further by mass directed auto-prep HPLC to give the title compound (6.4 mg).

Provenance & Evidence