Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 161117-83-5, name is tert-Butyl (2-methoxypyridin-3-yl)carbamate. A new synthetic method of this compound is introduced below., COA of Formula: C11H16N2O3
A) tert-butyl (4-benzyl-2-methoxypyridin-3-yl)carbamate [0412] To a solution of tert-butyl (2-methoxypyridin-3-yl)carbamate (25.1 g) and N,N,N’,N’-tetramethylethane-1,2-diamine (40.6 mL) in diethyl ether (374 mL) was added 1.6M n-butyllithium hexane solution (168 mL) at -78C, and the mixture was stirred under argon atmosphere at 0C for 1 hr. To the reaction mixture was added benzyl bromide (24.9 g) at -78C, and the mixture was stirred under argon atmosphere at room temperature for 4 hr. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution at room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/hexane), and crystallized from ethyl acetate and hexane to give the title compound (25.4 g). 1H NMR (300 MHz, CDCl3) delta 1.50 (9H, s), 3.96 (3H, s), 4.00 (2H, s), 5.99 (1H, brs), 6.60 (1H, d, J = 5.3 Hz), 7.12-7.33 (5H, m), 7.88 (1H, d, J = 5.3 Hz).
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Reference:
Patent; Takeda Pharmaceutical Company Limited; NARA, Hiroshi; DAINI, Masaki; KAIEDA, Akira; KAMEI, Taku; IMAEDA, Toshihiro; KIKUCHI, Fumiaki; EP2857400; (2015); A1;,
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