Water → 1-benzylazetidin-2-one

Participants

Reaction Steps

N-benzyl-2-azetidine carboxylic acid (2 mmol) was added slowly to excess oxalyl chloride at 0 degrees followed by gradual warming to 45 degrees (10 min.). The clear solution was then poured into cold, anhydrous ether, acidified with 10 drops of 70% perchloric acid and filtered to give N-benzyl-2-azetidinium perchlorate (95%). A suspension of this iminium salt in 10 ml of methylene chloride at 0 degrees was treated with 1 equivalent of 100% m-chloroperbenzoic acid followed by 2 equivalents of pyridine. The resulting reaction mixture was stirred for 40 min. and then poured into water. The organic layer was separated, washed with 5% NaHCO3 and dried over Na2SO4. Evaporation of the solvent under reduced pressure afforded N-benzyl-2-azetidinone as the sole product (70%).

Provenance & Evidence