Aniline → Methyl 1-(phenylcarbamoyl)cyclopropanecarboxylate

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Reaction Steps

Cyclopropane-1,1-dicarboxylic acid monomethyl ester (0.4 g, 2.78 mmol) was, dissolved in DMF (5.55 mL) and aniline (0.380 mL, 4.16 mmol) was added, followed by diisopropylethylamine (2.424 mL, 13.88 mmol) and O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (1.782 g, 5.55 mmol). The reaction mixture was stirred at room temperature for 18 hours and was then diluted with ethyl acetate (70 mL) and washed with 10% aqueous lithium chloride (3×40 mL), saturated aqueous ammonium chloride (40 mL), saturated aqueous sodium bicarbonate (40 mL) and brine (40 mL). The organic layer was dried over magnesium sulfate and evaporated to yield a dark brown oil. It was purified by silica gel chromatography (0 to 20% ethyl acetate/hexane) to yield methyl 1-(phenylcarbamoyl)cyclopropanecarboxylate (0.607 g, 100% yield) as a light peach solid. 1H NMR (400 MHz, DMSO-d6): δ 10.29 (s, 1H), 7.58 (d, 2H), 7.28 (t, 2H), 7.04 (t, 1H), 3.66 (s, 3H), 1.37 (m, 4H); MS (ESI) m/z: 220.1 (M+H+).

Provenance & Evidence