Sep-21 News Share a compound : 912444-89-4

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-tert-Butyl 4-ethyl 2,3,6,7-tetrahydro-1H-azepine-1,4-dicarboxylate, its application will become more common.

Synthetic Route of 912444-89-4,Some common heterocyclic compound, 912444-89-4, name is 1-tert-Butyl 4-ethyl 2,3,6,7-tetrahydro-1H-azepine-1,4-dicarboxylate, molecular formula is C14H23NO4, 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.

To a suspension of NaH (21.2 g, 0.318 mol, 60% dispersion in mineral oil) in DMSO (650 mL), S,S,S-trimethylsulfoxonium iodide (72.9 g, 0.331 mol) was added in small portions and stirred at rt for 1 h until gas evolution ceased. A solution of 1-tert-butyl 4-ethyl 2,3,6,7-tetrahydro-1H-azepine-1,4-dicarboxylate (9) (34.3 g, 0.127 mol) in DMSO (150 mL) was added dropwise and the reaction mixture was stirred at 50 C overnight. The resulting solution was cooled to rt, poured into ice-cold H2O (1 L) and extracted with t-BuOMe (3×700 mL). The combined organic extracts were washed with brine (3×500 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure. The product was purified by column chromatography (gradient hexane to hexane – t-BuOMe (7:3) as eluent). Yield: 19.8 g (55 %); colourless oil. 1H NMR(500 MHz, CDCl3): delta 4.14 – 4.06 (m, 2H), 3.98 – 3.78 (m, 2H), 3.10 (s, 1H), 2.96 (s, 1H), 2.77 (dd, J=15.3, 6.4 Hz, 1H), 2.36 (dt, J=14.1, 6.5 Hz, 1H), 1.75 – 1.65 (m, 1H), 1.49 (dd, J=9.2, 4.3 Hz, 1H), 1.43 (s, 9H), 1.37 – 1.26 (m, 2H), 1.23 (t, J=7.1 Hz, 3H), 0.77 (t, J=6.6, 4.3 Hz, 1H). 13C NMR(126 MHz, CDCl3): delta 175.4, 155.1, 79.3, 60.6, 47.6, 47.2, 32.7, 32.4, 28.4, 27.7, 26.9, 24.7, 14.2. MS (APCI): m/z = 284 [M+H]+. Anal. Calcd. for C15H25NO4: C 63.58; H 8.89; N 4.94. Found: C 63.86; H 8.58; N 5.13.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-tert-Butyl 4-ethyl 2,3,6,7-tetrahydro-1H-azepine-1,4-dicarboxylate, its application will become more common.

Reference:
Article; Yarmoliuk, Dmytro V.; Serhiichuk, Dmytro; Smyrnov, Vladyslav; Tymtsunik, Andriy V.; Hryshchuk, Oleksandr V.; Kuchkovska, Yuliya; Grygorenko, Oleksandr O.; Tetrahedron Letters; vol. 59; 52; (2018); p. 4611 – 4615;,
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