Trifluoroacetic acid → cis-4-(4-(Benzyloxy)phenyl)-3-fluoropiperidine

Participants

Reaction Steps

To a solution of cis-tert-butyl 4-(4-(benzyloxy)phenyl)-3-fluoropiperidine-1-carboxylate (400 mg, 1.04 mmol) in CH2Cl2 (4 mL) was dropwise added TFA (1 mL, 13 mmol) at rt. The mixture was stirred at rt for 2 h and then concentrated. To the residue was added 50 mL of saturated aqueous sodium bicarbonate and the mixture was extracted with 3×60 mL of CH2Cl2. The organic layer was dried over Na2SO4, filtered, and concentrated to dryness to yield 270 mg cis-4-(4-(benzyloxy)phenyl)-3-fluoropiperidine (0.95 mmol, 91%). (M+H)+=286.25. 1H NMR (500 MHz, chloroform-d) δ 7.49-7.38 (m, 4H), 7.34 (t, J=7.5 Hz, 1H), 7.26-7.20 (m, J=8.5 Hz, 2H), 7.01-6.93 (m, 2H), 5.08 (s, 2H), 4.70 (d, J=49.0 Hz, 1H), 3.38 (t, J=12.5 Hz, 1H), 3.25 (dt, J=13.4, 2.0 Hz, 1H), 2.93 (d, J=14.3 Hz, 1H), 2.90-2.68 (m, 3H), 2.09 (qd, J=12.9, 4.1 Hz, 1H), 1.69 (d, J=14.3 Hz, 1H).

Provenance & Evidence