Triphenylphosphine → HCID 58968716, compound

Participants

Reaction Steps

To a solution of tert-butyl 4-(2-(hydroxymethyl)-4-(trifluoromethyl)phenyl)-4-methoxypiperidine-1-carboxylate (410 mg, 1.05 mmol) in methylene chloride (7 mL) were added N-bromosuccinimide (342 mg; 1.92 mmol) and triphenylphosphine (516 mg; 1.96 mmol). The reaction was stirred at room temperature for 1 hour. The reaction was then purified over 40 g RediSep column (Teledyne Isco Inc. Lincoln Nebr.) (eluted with 5-30% ethyl acetate in heptane) to give 433 mg (90% yield) of a colorless oil. MS (ES+). Calc: 452.3 (81Br), Found: 407.2 (M(81Br)—HCO2−). 1H NMR (400 MHz, CDCl3) δ ppm 7.82 (d, J=1.66 Hz, 1H), 7.52 (dd, J=8.30, 1.66 Hz, 1H), 7.34, (d, J=8.30 Hz, 1H), 5.08 (s, 2H), 4.04 (d, J=12.86 Hz, 2H), 3.21 (t, J=12.86, 13.28 Hz, 2H), 3.02 (s, 3H), 2.26 (d, J=14.11 Hz, 2H), 1.86 (t, J=12.86, 14.11 Hz, 2H), 1.48 (s, 9H).

Provenance & Evidence