Citric Acid → 1-Isopropyl-4-(4-methoxybenzyl)-5-phenoxy-1,2-dihydro-3H-pyrazol-3-one

HRID 2102264Notes

Reaction equation

HRID 2102264 reaction equation
[BH4-].[Na+].C([O:10][C:11]1[C:15]([C:16](=O)[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[C:14]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:13]([CH:33]([CH3:35])[CH3:34])[N:12]=1)C1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[CH:33]([N:13]1[C:14]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:15]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[C:11](=[O:10])[NH:12]1)([CH3:34])[CH3:35]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 231133743-Benzyloxy-1-isopropyl-4-(4-methoxybenzoyl)-5-phenoxy-1H-pyrazole

Product 1

HCID 231133691-Isopropyl-4-(4-methoxybenzyl)-5-phenoxy-1,2-dihydro-3H-pyrazol-3-oneYield 54.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium borohydride (10 mg) was suspended in tetrahydrofuran (1 mL) and to the stirred suspension was added dropwise a solution of 3-benzyloxy-1-isopropyl-4-(4-methoxybenzoyl)-5-phenoxy-1H-pyrazole (24 mg) in tetrahydrofuran (4 mL) under ice cooling. The mixture was stirred at room temperature for 3 hours and 1 mL of 10% citric acid aqueous solution was added dropwise to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was sequentially washed with a saturated sodium hydrogen carbonate and brine. After the solution was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure and the obtained residue was dissolved in ethanol (5 mL). To the stirred solution was added 10% palladium carbon powder under ice cooling and the suspension was stirred at room temperature for 6 hours under hydrogen atmosphere at normal pressure. Insoluble material was removed by filtration and the solvent of filtrate was removed under reduced pressure to give the title compound (10 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was sequentially washed with a saturated sodium hydrogen carbonate and brine
  3. dry with materialAfter the solution was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. dissolutionthe obtained residue was dissolved in ethanol (5 mL)
  6. additionTo the stirred solution was added 10% palladium carbon powder under ice cooling
  7. stirringthe suspension was stirred at room temperature for 6 hours under hydrogen atmosphere at normal pressure
  8. customInsoluble material was removed by filtration
  9. customthe solvent of filtrate was removed under reduced pressure

Sources & evidence

ORD record
ord-83a0a84a050241069dfcb36f1c76bc83
Source dataset
uspto-grants-2009_08
Patent number
US07576064B2

Reaction notes

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