Some common heterocyclic compound, 78888-18-3, name is tert-Butyl allylcarbamate, molecular formula is C8H15NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. category: amides-buliding-blocks
Sodium hydride (768 mg of 60% dispersion in mineral oil, 19.2 mmol) was washed twice with 15 mL portions of hexane and suspended in 15 mL anhydrous THF. Reaction mixture was cooled to 0C and tert-butyl allylcarbamate (1.0 g, 6.4 mmol) was added dropwise. Reaction mixture was warmed up to room temperature and stirred under argon for 30 min. Reaction mixture was cooled to 0C and freshly distilled ethyl iodide (1.02 mL, 12.8 mmol) was added dropwise. Reaction mixture was allowed to warm up to room temperature overnight, and it was then cooled to 0C and quenched with saturated ammonium chloride solution. The layers were separated and aqueous layer was extracted with Et2O. Organics were combined and washed with saturated NaCl solution, dried over MgSO4 and concentrated under reduced pressure. Crude reaction mixture was purified by flash column chromatography (hexanes:EtOAc 4:1) to give 1.0g (85%) of the title compound as a colorless oil. IR (neat) 3083, 3010, 2979, 2933, 2249, 1682 cm-1; 1H NMR (300 MHz, CDCl3): delta [ppm] 1.03-1.07 (t, 3H, J=7.1 Hz), 1.42 (s, 9H), 3.20 (br m, 2H), 3.77 (br m, 2H), 5.05-5.11 (m, 2H), 5.68-5.81 (m, 1H); 13C NMR (75 MHz, CDCl3): delta [ppm] 12.59, 27.55, 40.39, 48.19, 78.31, 115.10, 133.67, 154.46; m/z (relative intensity) 185(1), 129(25), 112(9), 84(10), 70(30), 57(100), 41(65), 29(25). Anal.Calcd. for C10H19NO2: C, 64.83; H, 10.34; O, 17.24. Found: C, 64.67; H, 10.60; O, 17.31.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 78888-18-3, its application will become more common.
Reference:
Article; McMills, Mark C.; Humes, Ross J.; Pavlyuk, Oksana M.; Tetrahedron Letters; vol. 53; 7; (2012); p. 849 – 851;,
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