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. 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C12H21NO3
To a suspension of 60% sodium hydride dispersion (0.270 g, 6.75 mmol) in 20 mL DMSO, (lR,3r,5S)-tert-butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate (1.0 g, 4.399 mmol) was added. After stirring at room temperature for 20 min, l-(benzyloxy)-4-fluorobenzene (0.89 g, 4.401 mmol) was added and mixture was stirred at 90C (oil bath). After 2.5 d, dark mixture was extracted with water and AcOEt (3x). Combined organic phases were dried over MgS04, filtered, and concentrated. Residue (ca. 3 g) was dissolved in 40 mL CH2C12 and triethylamine (1 mL, 7.175 mmol) and di-teri-butyl dicarbonate (0.961 g, 4.401 mmol) were added. After 10 min, mixture was transferred into a separatory funnel and extracted with water and CH2C12. Organic phases was dried over MgSO/t, filtered, and concentrated. Residue was purified by Biotage column chromatography (Si02, hexane/ AcOEt gradient) to give (lR,3r,55)-teri-butyl 3-(4-(benzyloxy)phenoxy)-8- azabicyclo[3.2.1]octane-8-carboxylate (0.34 g, 0.830 mmol, 18.9%) as a white solid. Exact mass calculated for C25H31F6N04: 409.23, found: LCMS m/z = 410.2 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 1.47 (s, 9H), 1.93-1.97 (m, 4H), 2.07-2.17 (m, 4H), 4.49-4.53 (m, 2H), 4.50-4.52 (m, 1H), 5.01 (s, 2H), 6.75-6.77 (m, 2H), 6.89-6.91 (m, 2H), 7.31-7.43 (m, 5H).
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:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; BUZARD, Daniel J.; HAN, Sangdon; KIM, Sun Hee; LEHMANN, Juerg; ZHU, Xiuwen; WO2013/55910; (2013); A1;,
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