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

HRID 2084287

Reaktionsgleichung

Reaktionsgleichung von HRID 2084287
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-40979de8e77c46bfa21c32f05d5f3a59
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06716856B1

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