tert-Butyl 4-(4-(4-(benzyloxy)-4'-(trifluoromethyl)biphenyl-3-yl)pyridin-2-yl)piperazine-1-carboxylate → Tert-butyl 4-(4-(4-hydroxy-4'-(trifluoromethyl)biphenyl-3-yl)pyridin-2-yl)piperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 4-(4-(4-(benzyloxy)-4′-(trifluoromethyl)biphenyl-3-yl)pyridin-2-yl)piperazine-1-carboxylate (Preparation 115, 1.30 g, 2.20 mmol) was dissolved in ethanol (20 mL) at room temperature and palladium hydroxide on activated charcoal (130 mg) was added. The reaction mixture was heated at 60° C. under a hydrogen atmosphere (50 psi) for 18 hours. The mixture was then filtered through a pad of Celite™, rinsed with ethanol and concentrated in vacuo. The residue was purified on silica gel by Biotage (5% to 60% ethyl acetate in heptane over 20 CV). Further purification by reverse phase using acetonitrile/water (5/95-95/5) with 0.1% formic acid as eluent gave the title compound (650 mg, 59%) as a white powder.

Provenance & Evidence