Ammonium Chloride → HCID 89963614, compound

HRID 337820Notes

Reaction equation

HRID 337820 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:7][CH2:6][C:5](=[O:8])[C:4]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][CH:10]=2)=[CH:3]1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[CH3:1][C:2]1([CH3:15])[CH2:7][CH2:6][CH:5]([OH:8])[CH:4]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][CH:10]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 89962986HCID 89962986, compound

Product 1

HCID 89963614HCID 89963614, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the 4,4-dimethyl-2-(1-methyl-1H-pyrazol-5-yl)cyclohex-2-en-1-one (432 mg, 2.12 mmol) prepared in Example 67c 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 1 hour. To the reaction solution, a saturated aqueous solution of ammonium chloride (20 mL) was added, followed by extraction with dichloromethane (50 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate and vacuum concentrated to yield a mixture of the title compound and an allyl alcohol derivative.

Workup

  1. temperaturewith cooling on ice
  2. extractionfollowed by extraction with dichloromethane (50 mL)
  3. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate and vacuum
  4. concentrationconcentrated
  5. customto yield

Sources & evidence

ORD record
ord-3d151fe1da9d476195a572861cf8d907
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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