Isopropylamine → 3-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid isopropylamide

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Reaction Steps

A solution of trimethylaluminium (2 M in toluene, 1.02 mL, 2.0 mmol) was added dropwise (exothermic) to a solution of isopropyl amine (121 mg, 2.0 mmol) in dioxane (6 mL) and the resulting mixture was stirred at room temperature for 1 h. Then 3-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester (200 mg, 0.68 mmol) was added. The resulting mixture was then heated at 70° C. for 3 h and then cooled to room temperature and then poured into Seignette's salt and extracted with ethyl acetate which was then washed with brine, dried over sodium sulfate and evaporated. Purification by chromatography (silica, heptane:ethyl acetate=4:1 to 4:1) afforded the title compound (204 mg, 93%) which was obtained as a colourless oil. MS: m/e=322.4 [M+H]+.

Provenance & Evidence