Ammonium Chloride → HCID 89962805, compound

HRID 337830Notes

Reaction equation

HRID 337830 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:7][C:6](=[O:8])[C:5]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][CH:10]=2)=[CH:4][CH2:3]1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[CH3:1][C:2]1([CH3:15])[CH2:7][C@H:6]([OH:8])[C@@H:5]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 89962578HCID 89962578, compound

Product 1

HCID 89962805HCID 89962805, compoundYield 6.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the 5,5-dimethyl-2-(1-methyl-1H-pyrazol-5-yl)cyclohex-2-en-1-one (581 mg, 2.84 mmol) prepared in Example 72c in methanol (6.0 mL), sodium borohydride (200 mg, 5.29 mmol) was added with cooling on ice, and the reaction solution was stirred at room temperature for 30 minutes. To the reaction solution, a saturated aqueous solution of ammonium chloride (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=98:2) to yield the title compound (40 mg, 6.8%) 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=98:2)

Sources & evidence

ORD record
ord-29fcdb4f65954886b43d9482f3e1ab57
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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