Water → 1-(Diphenylmethyl)azetidin-3-one

Participants

Reaction Conditions

Reaction Steps

A three-neck flask was charged with oxalyl dichloride (10.6 mL, 119 mmol) and DCM (100.00 ml, 306 mmol), and the solution was cooled to −78° C. To the stirred solution was added, via dropping funnel, dimethylsulfoxide (16.9 mL, 238 mmol) in DCM (50 mL) over 30 min. The reaction was stirred at −78° C. for an additional 5 min, and then 1-benzhydrylazetidin-3-ol (25.90 g, 108 mmol) in DCM (50 mL) and DMSO (10 mL) was added dropwise over 5 min (T was maintained <−60° C.). The solution was stirred at −78° C. for an additional 20 min, and Et3N (75.3 mL, 541 mmol) was added slowly. The reaction was allowed to reach room temperature over 30 min and water (200 mL) was added. The mixture was extracted with EtOAc, washed with brine, dried over MgSO4 and evaporated. Purification by flash chromatography using 2% Et3N/hexanes gave 1-benzhydrylazetidin-3-one. 1H NMR (300 MHz, CDCl3) δ ppm 7.41-7.52 (m, 4H), 7.26-7.35 (m, 4H), 7.16-7.26 (m, 2H), 4.59 (s, 1H), 3.90-4.07 (m, 4H).

Provenance & Evidence