Ammonium Chloride → 2-(1-Methyl-1h-imidazol-5-yl)cyclohexan-1-ol

HRID 337790Notes

Reaction equation

HRID 337790 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[C:8](=[O:13])[CH2:9][CH2:10][CH2:11][CH:12]=2)=[CH:5][N:4]=[CH:3]1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[CH3:1][N:2]1[C:6]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]2[OH:13])=[CH:5][N:4]=[CH:3]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 899632992-(3-Methylimidazol-4-yl)cyclohex-2-en-1-one

Product 1

HCID 899633982-(1-Methyl-1h-imidazol-5-yl)cyclohexan-1-olYield 61.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the 2-(1-methyl-1H-imidazol-5-yl)cyclohex-2-en-1-one (80 mg, 0.454 mmol) prepared in Example 49a in methanol (2.0 mL), sodium borohydride (50 mg, 1.32 mmol) was added at room temperature, and the reaction solution was stirred at room temperature for 30 minutes. 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 the title compound (50 mg, 61%) in the form of a trans/cis (2:1) mixture as a colorless oil.

Workup

  1. extractionfollowed by extraction with dichloromethane (50 mL)
  2. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate and vacuum
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cb02b9af030046f4bfa6394f54e31ca1
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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