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

Participants

Reaction Conditions

Reaction Steps

Triethylamine (112.1 g, 1.11 mol) was added to a solution of N-diphenylmethylazetidin-3-ol (26.6 g, 0.11 mol) in DMSO (300 ml). The solution was cooled to 10° C. and a solution of sulphur trioxide-pyridine complex (112 g, 0.7 mol) in DMSO (500 ml) added, rapidly. Stirring was continued at 10° C. for 0.75 h and the mixture then warmed to 25° C. and stirred for 1 h. The solution was poured into ice-water (21) and extracted with EtOAc (3×1l). The combined extracts were washed with water (500 ml) and brine (500 ml) and dried (Na2SO4). The crude product was purified by chromatography through silica-gel eluting with petroleum ether/EtOAc (2:1) to give the desired ketone (25.8 g), mp 74°-75° C. δ (360 MHz, CDCl3) 4.00 (4H, s, 2 of CH2), 4.59 (1H, s, CH), 7.19-7.49 (10H, m, Ar--H).

Provenance & Evidence