Water → (1S*,2R*)-2-[1-(Tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]cyclohexanol

HRID 337764Notes

Reaction equation

HRID 337764 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][N:10]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.O.B1([O-])O[O:20]1.O.O.O.O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1>[O:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH:12]1[N:10]1[CH:11]=[C:7]([C@H:1]2[CH2:6][CH2:5][CH2:4][CH2:3][C@@H:2]2[OH:20])[CH:8]=[N:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrateHCID 899625894-Cyclohex-1-en-1-yl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole

Product 1

HCID 89962970(1S*,2R*)-2-[1-(Tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]cyclohexanolYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the 4-cyclohex-1-en-1-yl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole (775 mg, 3.34 mmol) prepared in Example 33a in THF (4 mL), a borane-THF complex (0.95 M; 3.4 mL, 3.23 mmol) was added with cooling on ice, and the reaction solution was stirred for 30 minutes with cooling on ice. To the reaction solution, a borane-THF complex (0.95 M; 3.4 mL, 3.23 mmol) was added again, and the mixture was stirred at room temperature for 90 minutes. To the reaction solution, water (5 mL) and subsequently sodium perborate tetrahydrate (1.00 g, 6.50 mmol) were added, and the mixture was stirred for 5 hours. To the reaction solution, sodium thiosulfate (2.0 g) was added, followed by extraction with ethyl acetate (50 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with column chromatography (dichloromethane/methanol=97:3) to yield the title compound (590 mg, 71%) as a colorless oil.

Workup

  1. temperaturewith cooling on ice
  2. temperaturewith cooling on ice
  3. additionTo the reaction solution, a borane-THF complex (0.95 M; 3.4 mL, 3.23 mmol) was added again
  4. stirringthe mixture was stirred at room temperature for 90 minutes
  5. stirringthe mixture was stirred for 5 hours
  6. extractionfollowed by extraction with ethyl acetate (50 mL)
  7. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  8. concentrationAfter vacuum concentration
  9. customthe residue was purified with column chromatography (dichloromethane/methanol=97:3)

Sources & evidence

ORD record
ord-26c09710a1564d44bf7454a890585887
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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