Water → HCID 58452902, compound

HRID 70615Notes

Reaction equation

HRID 70615 reaction equation
C(=O)([O-])[O-:2].[K+].[K+].[H-].COCCO[Al+]OCCOC.[Na+].[H-].[CH:21]1([CH2:26][CH:27]([C:36]2[NH:41][C:40](=[O:42])[C:39]([CH3:43])=[CH:38][CH:37]=2)[C:28]2[CH:33]=[CH:32][C:31]([S:34][CH3:35])=[CH:30][CH:29]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1.[OH2:44]>CC(C)=O.O>[CH:21]1([CH2:26][CH:27]([C:36]2[NH:41][C:40](=[O:42])[C:39]([CH3:43])=[CH:38][CH:37]=2)[C:28]2[CH:33]=[CH:32][C:31]([S:34]([CH3:35])(=[O:2])=[O:44])=[CH:30][CH:29]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 58452552HCID 58452552, compound

Product 1

HCID 58452902HCID 58452902, compound

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

Potassium carbonate (324 mg) and Oxone(R) (1.45 g) were sequentially added to a solution of 6-{2-cyclopentyl-1-[4-(methylsulfanyl)phenyl]ethyl}-3-methylpyridin-2(1H)-one (154 mg) in acetone-water (10 mL) under ice-cooling, and the mixture was stirred at 0° C. for 30 minutes. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=0:1) to give the title compound as a colorless amorphous (20 mg, 12%).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was then evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=0:1)

Sources & evidence

ORD record
ord-9a094355085c4d96a2c0336d6553b8e1
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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