Morpholine → [5-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-2H-pyrazol-3-yl]-morpholin-4-yl-methanone

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Reaction Steps

A solution of trimethylaluminium (2 M in toluene, 0.92 mL, 1.3 mmol) was added dropwise (exothermic) to a solution of morpholine (111 μL, 1.3 mmol) in dioxane (3 mL) and the resulting mixture was stirred at room temperature for 1 h. Then a solution of 5-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid methyl ester (100 mg, 0.32 mmol) in dioxane (2 mL) was added. The resulting mixture was heated at 90° C. overnight and then cooled to room temperature and then poured into Seignette's salt solution and extracted with ethyl acetate which was then washed with brine, dried over sodium sulfate and evaporated. Purification by chromatography (silica, dichloromethane:methanol=9:1) afforded the title compound (47 mg, 40%), which was obtained as a colorless oil. MS: m/e=369.1 [M+H]+.

Provenance & Evidence