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., Safety of tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate
General procedure: . Following GP1, under N2 atmosphere, to a 0C. solution of tert-butyl (1R,3r,5S)-3-hydroxybicyclo[3.2.1]octane-8-carboxylate (0.15 g, 1 eq., 0.66 mmol), phenol (0.07 g, 1.2 eq., 0.79 mmol), and PPh3 (0.21 mg, 1.5 eq., 0.99 mmol) in dry THF (5 mL) was added dropwise diisopropyl azodicarboxylate (0.2 mL, 1.2 eq., 0.79 mmol). The reaction crude was allowed to warm to room temperature and stirred for 16 h. Then, the mixture was quenched with HCl (10 mL) and extracted with EtOAc (25 mL). The organic extracts were washed with brine (10 mL), dried over Na2SO4 and concentrated in vacuo to furnish the crude product, which was purified by flash chromatography eluting with cyclohexane/EtOAc (0 to 80%) to give the pure title compound as colourless oil (0.07 g, 40%). UPLC-MS (method A): Rt. 1.86 min (TIC); ionization ES+304 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta 7.30-7.23 (m, 2H), 7.01-6.95 (m, 2H), 6.92 (td, J=7.3, 1.1Hz, 1H), 4.85-4.74 (m, 1H), 4.19-4.10 (m, 2H), 2.15-2.03 (m, 2H), 1.95-1.73 (m, 4H), 1.58-1.46 (m, 2H), 1.42 (s, 9H), 1.40-1.37 (m, 1H).
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; FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA; BERTOZZI, Fabio; BANDIERA, Tiziano; PONTIS, Silvia; REGGIANI, Angelo; GIACOMINA, Francesca; DI FRUSCIA, Paolo; US2019/135778; (2019); A1;,
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