Trifluoroacetic acid → 1-Benzhydryl-3-(3-methylbenzofuran-2-yl)azetidine

Participants

Reaction Steps

To a cooled (0° C.) solution of 1-benzhydryl-3-(3-methylbenzofuran-2-yl)azetidin-3-ol (406 mg, 1.099 mmol) in dichloromethane (50 mL) were added triethylsilane (1.775 mL, 10.99 mmol) and trifluoroacetic acid (1.630 mL, 22.01 mmol). The reaction mixture was warmed to rt and stirred for 23 h. After 18 h, boron trifluoride etherate (0.6 mL, 4.73 mmol) was added and the reaction was allowed to stir for an additional 5 h. The reaction mixture was partitioned between sat. NaHCO3 and DCM. The layers were separated, the organic layer was washed with sat. NaHCO3 and brine, dried on Na2SO4 and concentrated. The residue was purified by flash chromatography (heptane/EtOAc, 0%->30%), yielding the title product (244 mg, 63%) as an off-white solid.

Provenance & Evidence