1-(Diphenylmethyl)azetidin-3-yl methanesulfonate → 3-Amino-1-(diphenylmethyl)azetidine

Participants

Reaction Steps

3-Mesyloxy-1-benzhydrylazetidine (30.32 g, 95.5 mmol), potassium phthalimide (21.59 g, 116.53 mmol) and hexadecyl tributylphosphonium bromide (5.92 g, 11.7 mmol) were added to toluene (600 mL) and the mixture stirred at room temperature overnight. The reaction was then heated at reflux for 3 h. The solid was removed by filtration, washed with EtOAc and the combined organics then washed with H2O. After drying over Na2SO4, the organics were treated with charcoal and then concentrated to an oil. Addition of isopropyl ether induced crystallization of the product (16.37 g, 46%).

Provenance & Evidence