Hydrochloric Acid → HCID 178439090, compound

HRID 598796Notes

Reaction equation

HRID 598796 reaction equation
[CH:1]([C:4]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[N:6]([CH:12]2[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)[N:5]=1)([CH3:3])[CH3:2].[BH4-].[Na+].Cl>CO.CCOC(C)=O>[CH:1]([C:4]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[N:6]([C@H:12]2[CH2:13][CH2:14][C@H:15]([OH:18])[CH2:16][CH2:17]2)[N:5]=1)([CH3:2])[CH3:3].[CH:1]([C:4]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[N:6]([C@@H:12]2[CH2:13][CH2:14][C@H:15]([OH:18])[CH2:16][CH2:17]2)[N:5]=1)([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 58256798HCID 58256798, compound

Product 2

HCID 178439090HCID 178439090, compoundHCID 178439091HCID 178439091, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(3,5-diisopropyl-pyrazol-1-yl)-cyclohexanone (236 mg, 0.95 mmol) in methanol (10 mL) was added NaBH4 (38 mg, 1 mmol). The reaction was stirred at room temperature overnight followed by acidification with HCl (10% aqueous). The reaction was diluted with EtOAc and extracted with water, brine, dried over MgSO4 and concentrated. The residue was purified on silica gel (100% hexane to 4:1 hexane:EtOAc) to give trans-4-(3,5-diisopropyl-pyrazol-1-yl)-cyclohexanol (yield 43.3 mg) and cis-4-(3,5-diisopropyl-pyrazol-1-yl)-cyclohexanol (yield 121 mg) as colorless solids. LC-MS (C15H26N2O calculated 250) m/z 251 (M+H).

Workup

  1. extractionextracted with water, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified on silica gel (100% hexane to 4:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-4c866812a6b04219b4e6f80d861c2c02
Source dataset
uspto-grants-2011_03
Patent number
US07897634B2

Reaction notes

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