1-(Diphenylmethyl)azetidin-3-one → 1-Benzhydryl-3-methylazetidin-3-ol

Participants

Reaction Steps

1-Benzhydryl-azetidin-3-one (335 mg) in diethyl ether (6.0 mL) was treated with 3.0 M methylmagnesium bromide in diethyl ether (0.52 mL) at 0° C., stirred for 10 minutes and quenched with saturated aqueous sodium bicarbonate. The solution was then extracted with methylene chloride (×3), and the combined organics were dried over magnesium sulfate, and concentrated to provide 363 mg of the title compound as a clear, colorless oil. 1H NMR (CDCl3, 300 MHz) δ ppm 1.53 (s, 3H), 1.96 (s, 1H), 1.96 (d, 2H, J=8.42 Hz), 3.19 (d, 2H, J=8.42 Hz), 4.34 (s, 1H), 7.17 (m, 2H), 7.26 (m, 2H), 7.31 (m, 2H), 7.40 (m, 4H).

Provenance & Evidence