Reference of 1871-57-4, A common heterocyclic compound, 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, molecular formula is C4H6Cl2, its 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.
Sodium hydride (60% in mineral oil) (0.92 g, 23.05 mmol) was dissolved in DMF (20 mL) at 0 C and 3-chloro-2-(chloromethyl)prop-1-ene (0.81 mL, 7.68 mmol) was added in portions. Separately, tert-butyl N-[2-(tert-butoxycarbonylamino)ethyl]carbamate (2.00 g, 7.68 mmol) was dissolved in THF (20 mL) and added. The reaction mixture was stirred at 20 C for 3 h. The volatiles were removed under reduced pressure. The reaction was diluted with water (50 mL) and then extracted with EtOAc (3 x 80 mL). The organic extracts were combined passed through a phase separation cartridge and the volatiles were removed under reduced pressure. The crude product was dissolved in DCM and purified via silica gel chromatography eluting with 0-50% EtOAc in heptane to afford di-tert-butyl 6-methylene-1,4-diazepane-1,4-dicarboxylate 28 (1.01 g, 42%) as a white solid. 1H NMR (400 MHz, CDCl3) 1.39-1.5 (m, 18H), 3.39-3.56 (m, 4H), 3.80 – 4.06 (m, 4H), 4.86 – 5.13 (m, 2H); 13C NMR (400 MHz, DMSO, 100 C) 28.58, 48.49, 52.21, 79.50, 111.89, 144.82, 154.74; HRMS [M+H]+ measured 335.1940, C16H28N2O4 requires 335.1947.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Article; Watson, David W.; Gill, Matthew; Kemmitt, Paul; Lamont, Scott G.; Popescu, Mihai V.; Simpson, Iain; Tetrahedron Letters; vol. 59; 51; (2018); p. 4479 – 4482;,
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