cis-4-(4-(Benzyloxy)phenyl)-3-fluoropiperidine → cis-4-(3-Fluoropiperidin-4-yl)phenol

Participants

Reaction Steps

To 10% Pd/C (40 mg) under nitrogen was added a solution of cis-4-(4-(benzyloxy)phenyl)-3-fluoropiperidine (140 mg, 0.49 mmol) in IPA (4 mL). The mixture was stirred under a hydrogen atmosphere using balloon pressure at rt for 2 h. The Pd/C was removed by filtration through a glass fiber filter. The filtrate was concentrated to give cis-4-(3-fluoropiperidin-4-yl)phenol (90 mg, 0.46 mmol, 94% yield). LC/MS (Method J, M+H)+=196.25, RT=0.706 min; 1H NMR (500 MHz, methanol-d4) δ 7.14 (d, J=8.4 Hz, 2H), 6.74 (d, J=8.7 Hz, 2H), 4.63 (d, J=48.4 Hz, 1H), 3.30-3.22 (m, 1H), 3.15 (dt, J=13.1, 2.0 Hz, 1H), 2.95-2.66 (m, 3H), 2.12 (qd, J=13.0, 4.2 Hz, 1H), 1.64 (dd, J=13.4, 3.0 Hz, 1H).

Provenance & Evidence