Electric Literature of 28539-02-8, 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. 28539-02-8, name is 1-(Hydroxymethyl)benzotriazole. A new synthetic method of this compound is introduced below.
To a stirred solution of n-butyllithium(1.6 M) (4.67 mL, 7.47 mmol) in anhydrous THF (15 mL) was added dropwise 2,2,6,6-tetramethylpiperidine (1.05 g, 7.47 mmol) at -10 C. The solution was allowed to stirred at 0 C for 30 minutes then cooled to -78 C. 2-((3-fluoro-2- methylphenoxy)methyl)-5-hydroxy-2-methyl-7-morpholinochroman-4-one (1.0 g, 2.49 mmol) in anhydrous THF (10 mL) was added dropwise and stirred for an additional 1 hour. 1 H-benzotriazole- methanol (0.55 g, 3.74 mmol) in anhydrous THF (20 mL) was added dropwise over a period of 30 minutes and kept 2 hours at this temperature. The reaction was quenched with Sat.NH4CI and diluted with ethyl acetate (50 mL). The organic layer was dried over Na2S04, filtered, and concentrated in vacuo. The crude compound was purified by Grace column chromatography (C-18 Reverse phase column), using 60% (0.1 % FA) acetonitrile in (0.1 % FA) water as an eluent to afford 92 (430 mg, 40%) as an off white solid. lsomer-92-1 : 1H NMR (300 MHz, DMSO-tf6):512.01 (bs, 1 H), 7.21 -7.1 1 (m, 1 H), 6.85-6.71 (m, 2H), 5.97 (d, J = 2.1 Hz, 1 H), 5.92 (d, J = 2.1 Hz, 1 H), 4.85 (t, J = 5.4 Hz, 1 H), 4.28 – 4.15 (m, 2H), 3. 87 – 3.75 (m, 2H), 3.64 (t, J = 4.5 Hz, 4H), 3.29 (t, J = 4.5 Hz, 4H), 2.91 (t, J = 5.4 Hz, 1 H), 1.95 (d, J = 1.8 Hz, 3H), 1.58 (s, 3H) lsomer-92-2: 1H NMR (300 MHz, DMSO-tf6):512.02 (bs, 1 H), 7.21 -7.1 1 (m, 1 H), 6.85-6.71 (m, 2H), 5.97 (d, J = 2.1 Hz, 1 H), 5.92 (d, J = 2.1 Hz, 1 H), 4.81 (t, J = 5.7 Hz, 1 H), 4.28 – 4.15 (m, 2H), 3. 87 – 3.75 (m, 2H), 3.64 (t, J = 4.5 Hz, 4H), 3.29 (t, J = 4.5 Hz, 4H), 2.91 (t, J = 5.4 Hz, 1 H), 1.95 (d, J = 1.8 Hz, 3H), 1.58 (s, 3H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound,28539-02-8, 1-(Hydroxymethyl)benzotriazole, and friends who are interested can also refer to it.
Reference:
Patent; GVK BIOSCIENCES PRIVATE LIMITED; JOSHI, Hemant; DURAISWAMY, Athisayamani Jeyaraj; BETHI, Reddy Sridhar; ROY, Chowdhury Arnab; (89 pag.)WO2017/90002; (2017); A2;,
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