156731-40-7, name is 1-(Boc-amino)-3-butene, belongs to amides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C9H17NO2
Sodium hydride (583 mg of 60% dispersion in mineral oil, 14.6 mmol) was washed twice with 16 mL portions of hexane and suspended in 16 mL anhydrous THF. Reaction mixture was cooled to 0C and tert-butyl but-3-enylcarbamate (830 mg, 4.85 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 (0.78 mL, 9.7 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 900 mg (93%) of the title compound as a colorless oil. IR (neat) 3078, 2976, 2932, 2871, 1685 cm-1; 1H NMR (300 MHz, CDCl3): delta [ppm] 1.04-1.09 (t, 3H, J=7.1 Hz), 1.42 (s, 9H), 2.20-2.27 (m, 2H), 3.19 (br m, 4H), 4.95-5.06 (m, 2H), 5.67-5.81 (m, 1H); 13C NMR (75 MHz, CDCl3): delta [ppm] 11.58, 26.45, 31.25, 39.90, 44.32, 77.01, 114.33, 133.62, 153.36; m/z (relative intensity) 199(1), 158(5), 102(8), 57(100), 41(70), 29(52). Anal.Calcd. for C11H21NO2: C, 66.29; H, 10.62; O, 16.06. Found: C, 66.07; H, 10.66; O, 15.95.
The synthetic route of 156731-40-7 has been constantly updated, and we look forward to future research findings.
Reference:
Article; McMills, Mark C.; Humes, Ross J.; Pavlyuk, Oksana M.; Tetrahedron Letters; vol. 53; 7; (2012); p. 849 – 851;,
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