Reference of 143557-91-9,Some common heterocyclic compound, 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, molecular formula is C12H21NO3, 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.
After dissolving (endo)-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (CAS 143557-91-9) (2.00 g) and 1-(3-chloropropyl)-2-fluorobenzene (CAS 110406-96-7) (1.67 g) in N,N-dimethylformamide (10 ml), tetra-n-butylammonium iodide (325 mg) was added to the solution. Sodium hydride (60% in oil) (422 mg) was added and the mixture was stirred at room temperature for 17 hours and 30 minutes. Sodium hydride (60% in oil) (352 mg) was added to the reaction mixture, and stirring was continued for 2 hours at room temperature. Water was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was washed with a saturated aqueous solution of ammonium chloride, water and brine in that order and then dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (1.20 g).1H-NMR (400 MHz, CDCl3); delta 1.46 (s, 9H), 1.81-1.95 (m, 8H), 2.06-2.11 (m, 2H), 2.71-2.75 (m, 2H), 3.37-3.38 (m, 2H), 3.54-3.56 (m, 1H), 4.10-4.18 (m, 2H), 6.98-7.07 (m, 2H), 7.14-7.21 (m, 2H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, its application will become more common.
Reference:
Patent; Eisai R&D Management Co., Ltd.; US2009/270369; (2009); A1;,
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