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

HRID 985470Notes

Reaction equation

HRID 985470 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)[N:20]2[CH2:23][CH:22]([S:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:21]2)=[CH:15][CH:14]=1>ClCCl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:31]2[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=2)[N:20]2[CH2:21][CH:22]([S:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:9])[CH2:23]2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22506808HCID 22506808, compound

Product 1

HCID 225067291-[bis(4-chlorophenyl)methyl]-3-[(RS)-phenylsulfinyl]azetidineYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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)].

Workup

  1. washthe reaction mixture is washed with 30 cm3 of a saturated sodium hydrogen carbonate solution
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. washAfter 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
  6. customcollecting 60-cm3 fractions, fractions 9 to 16
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-4542f5006e494fdb8a3a03fa1f99e4d9
Source dataset
uspto-grants-2005_03
Patent number
US06872717B2

Reaction notes

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