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

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Reaction Steps

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.

Provenance & Evidence