Methanol → 2-acetamido-N-tert-butyl-2-(2-(pyridin-2-yl)ethyl)hex-5-enamide

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A solution of 1-(pyridin-2-yl)hept-6-en-3-one (825 mg, 4.36 mmol) and ammonium acetate (1.01 g, 13.09 mmol) in 2,2,2-trifluoroethanol (3 mL) was treated with tert-butyl isocyanide (730 mg, 0.99 mL, 8.80 mmol). After stirring at room temperature for 6 days, the reaction mixture was purified by flash column chromatography (crude reaction mixture loaded on the top of the column; silica gel, 0-10% methanol in dichloromethane) to give 2-acetamido-N-tert-butyl-2-(2-(pyridin-2-yl)ethyl)hex-5-enamide as white solid (1.37 g, 95%). ESI MS found for C19H29N3O2 m/z [332.2 (M+1)].

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