Water → 1-(Diphenylmethyl)-3-(pentylsulfonyl)azetidine

Participants

Reaction Steps

To a solution of 1-(diphenylmethyl)-3-(pentylthio)azetidine (228 mg, 0.70 mmol; which may be prepared as described in Step 2) in methanol (6.3 mL) and water (6.3 mL) was added H2SO4 1N (0.7 mL). The reaction mixture was stirred for 10 minutes, then oxone (1.08 g, 1.75 mmol) was added and the mixture stirred at room temperature for 12 h. A solution of saturated NaHCO3 (5 mL) was added and the mixture extracted with ethyl acetate. The two layers were separated and the organic washed with brine, dried over Na2SO4, filtered and concentrated. The crude was then purified on column chromatography (pentane/EtOAc, 100/0 then 90/10) to give the title product (75 mg, 30%) as a pale yellow oil. The less pure fraction (N-oxide) can be recycled in hydrogenolysis conditions.

Provenance & Evidence