Trifluoroacetic acid → HCID 118207450, compound

Participants

Reaction Steps

To a solution of tert-butyl 3-hydroxy-3-(4-methoxyphenyl)azetidine-1-carboxylate (1.1 g, 3.9 mmol) in DCM (15 mL) at 0° C. was added triethylsilane (5 mL, 31 mmol) followed by TFA (1 mL, 13.8 mmol). The reaction mixture was allowed to warm to rt and stirred overnight. The mixture was then diluted with a satd. sodium bicarbonate solution and extracted with DCM (100 mL). The organic layer was separated, dried over Na2SO4, filtered, and evaporated under reduced pressure to give a crude product which was purified by silica gel chromatography eluting with 10% ethyl aceate in hexane to give pure tert-butyl 3-(4-methoxyphenyl)azetidine-1-carboxylate (380 mg, 1.37 mmol, 34.8% yield). LCMS (Method 107): (ES-API), m/z 264.0 (M+H) RT=2.128 min; 1H NMR (400 MHz, DMSO-d6) δ 7.31-7.20 (m, 2H), 6.96-6.87 (m, 2H), 4.27-4.17 (m, 2H), 3.82-3.69 (m, 6H), 1.41 (s, 9H).

Provenance & Evidence