m-Chloroperbenzoic acid → 1-[bis(4-chlorophenyl)methyl]-3-[(RS)-phenylsulfinyl]azetidine

Participants

Reaction Steps

0.25 g of meta-chloroperbenzoic acid is added at room temperature to a solution of 0.40 g of 1-[bis(4-chlorophenyl)methyl]-3-(phenylsulfanyl)azetidine in 20 cm3 of dichloromethane. After stirring for 3 hours at room temperature, the reaction mixture is washed with 30 cm3 of a saturated sodium hydrogen carbonate solution, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). After chromatography on a silica gel column (particle size 0.06-0.200 mm, height 25 cm, diameter 2 cm), eluting under an argon pressure of 0.8 bar with an ethyl acetate/cyclohexane 20/80 by volume mixture and collecting 60-cm3 fractions, fractions 9 to 16 are combined and concentrated to dryness under reduced pressure (2.7 kPa), taken up in heptane in order to isolate 100 mg of 1-[bis(4-chlorophenyl)methyl]-3-[(RS)-phenylsulfinyl]azetidine in the form of a white solid [1H NMR spectrum (300 MHz, CDCl3, δ in ppm): 3.01 (broad t, J=7.5 Hz: 1H); 3.32 (broad t, J=7.5 Hz 1H); 3.45 (broad t, J=7.5 Hz: 2H); 3.59 (mt: 1H); 4.45 (broad s,: 1H); from 7.15 to 7.65 (mts: 13H)].

Provenance & Evidence