Cyclohexane → 4-Hydroxy-1-(2-pyridyl)-3,6,6-trimethyl-4,5,6,7-tetrahydroindazole

HRID 2084287Notes

Reaction equation

HRID 2084287 reaction equation
[BH4-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:17]2[CH2:16][C:15]([CH3:19])([CH3:18])[CH2:14][C:13](=[O:20])[C:12]=2[C:11]([CH3:21])=[N:10]1.C1CCCCC1>C(O)C>[OH:20][CH:13]1[CH2:14][C:15]([CH3:19])([CH3:18])[CH2:16][C:17]2[N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=3)[N:10]=[C:11]([CH3:21])[C:12]1=2

Participants

5

Reactant 3

HCID 8078CyclohexaneHCID 41652463,6,6-Trimethyl-1-pyridin-2-yl-5,7-dihydroindazol-4-oneHCID 4311764Sodium borohydride2×

Product 1

HCID 98165614-Hydroxy-1-(2-pyridyl)-3,6,6-trimethyl-4,5,6,7-tetrahydroindazoleYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.09 g (2.36 mol) of sodium borohydride were added portionwise to the solution of 1-(2-pyridyl)-3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydroindazole (0.3 g, 1.18 mmol), prepared as described in example 3, in ethanol (15 ml) maintained under inert atmosphere and under magnetic stirring at room temperature. After about 20 hours, additional sodium borohydride (0.09 g) was added and the reaction mixture was heated at about 50° C. for about 8 hours. The solvent was evaporated and the residue was diluted with water and extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and evaporated to give a foam which was treated with cyclohexane and filtered to yield the title compound as a colourless solid (0.2 g, 66%): m.p. 125-126° C.

Workup

  1. customprepared
  2. temperaturemaintained under inert atmosphere
  3. temperaturethe reaction mixture was heated at about 50° C. for about 8 hours
  4. customThe solvent was evaporated
  5. additionthe residue was diluted with water
  6. extractionextracted with dichloromethane
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. customevaporated
  9. customto give a foam which
  10. filtrationfiltered

Sources & evidence

ORD record
ord-40979de8e77c46bfa21c32f05d5f3a59
Source dataset
uspto-grants-2004_04
Patent number
US06716856B1

Reaction notes

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