Water → HCID 89962354, compound

HRID 337869Notes

Reaction equation

HRID 337869 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:6][C:5](=[O:7])[CH:4]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][CH:9]=2)[CH2:3]1.[BH4-].[Na+].O>CO>[CH3:1][C:2]1([CH3:14])[CH2:6][C@H:5]([OH:7])[C@@H:4]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][CH:9]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 89963119HCID 89963119, compound

Product 1

HCID 89962354HCID 89962354, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the 4,4-dimethyl-2-(1-methyl-1H-pyrazol-5-yl)cyclopentanone (750 mg, 3.90 mmol) prepared in Example 93d in methanol (8.0 mL), sodium borohydride (150 mg, 3.97 mmol) was added with cooling on ice, and the reaction solution was stirred at room temperature for 1 hour. To the reaction solution, water (50 mL) was added, followed by extraction with ethyl acetate (100 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=97:3) to yield the title compound (390 mg, 52%) as a colorless oil.

Workup

  1. temperaturewith cooling on ice
  2. extractionfollowed by extraction with ethyl acetate (100 mL)
  3. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  4. concentrationAfter vacuum concentration
  5. customthe residue was purified with silica gel chromatography (dichloromethane/methanol=97:3)

Sources & evidence

ORD record
ord-a9adb5f3fb1843c697beda1f04dd8fb0
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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