1-(Diphenylmethyl)azetidin-3-yl methanesulfonate → 2-[1-(diphenylmethyl)azetidin-3-yl]-1H-isoindole-1,3(2H)-dione

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.362 mol of 1-benzhydryl-3-mesyloxyazetidine (J. Org. Chem. 1972, 37, 3953-3955), 0.44 mol of potassium phthalimide and 0.045 mol of hexadecyltributylphosphonium bromide in 500 ml of anhydrous toluene is heated at reflux for 5 hours, then it is cooled at 20° C. The precipitate is filtered, washed with 400 ml of ethyl acetate and discarded. The organic solution is washed with water, dried on anhydrous sodium sulfate, filtered on charcoal and concentrated under reduced pressure. The oily residue is crystallized from 600 ml of diisopropyl ether. Thus, 80 g (Yield: 67.4% of the theoretic) of 1-benzhydryl-3-phthalimidoazetidine are obtained; m.p. 118°-120° C.

Provenance & Evidence