1-Benzhydryl-3-(4-fluorophenoxy)azetidine → 3-(4-Fluorophenoxy)azetidine

Participants

Reaction Steps

Palladium hydroxide (500 mg) and 1-(diphenylmethyl)-3-(4-fluorophenoxy)azetidine (500 mg, 1.50 mmol) were combined in ethanol (50 mL) and hydrogenated at 50 psi for 18 h. The reaction mixture was then filtered through Celite and concentrated in vacuo. The residue was purified via silica gel chromatography (Eluant: 00:5:2 chloroform:MeOH: concentrated aqueous ammonium hydroxide) to provide C40. Yield: 188 mg, 1.12 mmol, 75%. LCMS m/z 168.1 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.44 (br s, 1H), 3.76 (m, 2H), 3.89 (m, 2H), 4.91 (m, 1H), 6.66 (m, 2H), 6.93 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 4.55, 70.81, 115.43, 115.51, 115.76, 115.99, 152.96, 156.15, 158.53.

Provenance & Evidence