Water → HCID 89962695, compound

HRID 337901Notes

Reaction equation

HRID 337901 reaction equation
C([O:9][C@H:10]1[CH2:14][C:13]([F:16])([F:15])[CH2:12][C@@H:11]1[C:17]1[N:21]([CH3:22])[N:20]=[CH:19][CH:18]=1)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].O>CO>[F:16][C:13]1([F:15])[CH2:14][C@H:10]([OH:9])[C@@H:11]([C:17]2[N:21]([CH3:22])[N:20]=[CH:19][CH:18]=2)[CH2:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 89962468HCID 89962468, compound

Product 1

HCID 89962695HCID 89962695, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the (1S*,2R*)-4,4-difluoro-2-(1-methyl-1H-pyrazol-5-yl)cyclopentyl benzoate (90 mg, 0.294 mmol) prepared in Example 107d in methanol (3.0 mL), potassium carbonate (60 mg, 0.434 mmol) was added, and the reaction solution was stirred for 30 minutes. To the reaction solution, water (10 mL) was added, and an organic layer was extracted with ethyl acetate (20 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (dichloromethane/methanol=96:4) to yield the title compound (48 mg, 81%) as a colorless oil.

Workup

  1. extractionan organic layer was extracted with ethyl acetate (20 mL)
  2. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  3. concentrationAfter vacuum concentration
  4. customthe residue was purified with silica gel chromatography (dichloromethane/methanol=96:4)

Sources & evidence

ORD record
ord-fa1dad45489146028d9e658aa1ec498f
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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