Aniline → Methyl 1-(phenylcarbamoyl)cyclopropanecarboxylate

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+).

1. washwashed with 10% aqueous lithium chloride (3×40 mL), saturated aqueous ammonium chloride (40 mL), saturated aqueous sodium bicarbonate (40 mL) and brine (40 mL)
2. dry with materialThe organic layer was dried over magnesium sulfate
3. customevaporated
4. customto yield a dark brown oil
5. customIt was purified by silica gel chromatography (0 to 20% ethyl acetate/hexane)

ORD record

ord-7d80cb4f304b4eaebb2fdce3e20eb167

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637672B2