m-Chloroperbenzoic acid → HCID 59577235, compound

HRID 2042003Notes

Reaction equation

HRID 2042003 reaction equation
[C:1]([C:5]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:6]=1[O:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:24])[CH2:15][S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[OH:23])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:38])C=1.S(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[C:1]([C:5]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:6]=1[O:7][CH:8]1[CH2:9][CH2:10][N:11]([C:14](=[O:24])[CH2:15][S:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[OH:23])=[O:38])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 59577054HCID 59577054, compound

Product 1

HCID 59577235HCID 59577235, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-({2-[4-(2-tert-butyl-4-fluorophenoxy)piperidin-1-yl]-2-oxoethyl}sulfanyl)phenol (292 mg, 0.70 mmol) obtained in Example 239 and m-chloroperbenzoic acid (275 mg, 1.12 mmol) in ethyl acetate (14 mL) was stirred at 0° C. for 3 hr. Saturated aqueous sodium bisulfite solution (5 mL) was added to the reaction mixture, and the mixture was stirred at room temperature for 30 min. The reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate 90:10-20:80) to give 2-({2-[4-(2-tert-butyl-4-fluorophenoxy)piperidin-1-yl]-2-oxoethyl}sulfinyl)phenol (163 mg, 54%) as a white solid.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate 90:10-20:80)

Sources & evidence

ORD record
ord-0b3b5fa643ed4e3c9a50bac09d1b3edf
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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