Methanol tetrahydrofuran water → HCID 66879138, compound

HRID 907516Notes

Reaction equation

HRID 907516 reaction equation
[CH:1]1([C:6]2[CH2:10][CH2:9][C:8](=[O:11])[C:7]=2[C:12]2[CH:17]=[CH:16][CH:15]=[C:14](SC)[CH:13]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O[O:21][S:22]([O-:24])=O.[K+].[CH2:26]1COCC1.CO.O>>[CH:1]1([C:6]2[CH2:10][CH2:9][C:8](=[O:11])[C:7]=2[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([S:22]([CH3:26])(=[O:24])=[O:21])[CH:17]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 3

HCID 21892291Methanol tetrahydrofuran waterHCID 23707502Potassium hydroxy sulfiteHCID 66879033HCID 66879033, compound

Product 1

HCID 66879138HCID 66879138, compound

Procedure

To a solution of 120 mg 3-cyclopentyl-2-(3-methylthiophenyl)-2-cyclopenten-1-one in 12 ml 1:1:1 mixture of THF/methanol/water, was added 800 mg OXONE®, and the reaction mixture was stirred for 3 hours. Then the reaction mixture was concentrated under reduced pressure and extracted with water/ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography (silica gel, hexane/ethyl acetate=3:1) to yield 120 mg 3-cyclopentyl-2-(3-methylsulfonylphenyl)-2-cyclopenten-1-one. The methylsulfone compound was condensed with hydroxylamine hydrochloride according to a procedure similar to that described in STEP 4 for Example 1 to afford 80 mg of 3-cyclopentyl-2-(3-methylsulfonylphenyl)-2-cyclopenten-1-one oxime as a solid. mp=164-165° C.; 1H NMR (CDCl3, 300 MHz): δ 7.90-7.85 (m, 2H), 7.62-7.52 (m, 2H), 7.19 (bs, 1H), 3.08 (s, 3H), 2.85 (m, 1H), 2.80 (m, 2H), 2.64 (m, 2H), 1.73 (m, 4H), 1.58 (m, 4H); APCI MS: m/z 320.1 (M+1).

Workup

  1. concentrationThen the reaction mixture was concentrated under reduced pressure
  2. extractionextracted with water/ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by column chromatography (silica gel, hexane/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-ad87fca472b740e1ad6f27f5db7ebbf1
Source dataset
uspto-grants-2011_09
Patent number
US08013187B2

Reaction notes

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