Category: 143557-91-9

Synthetic Route 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.

To a solution of (trans)-3-hydroxy-8-aza-bicyclo [3.2. 1] [OCTANE-8-CARBOXYLIC] acid tert-butyl ester (2.3 grams, 10.1 [MMOL)] in tetrahydrofuran (50 ml) was added 4- fluoro phenol (1.75 grams, 15.6 mmol), triphenyl phosphine (4.02 grams, 15.3 [MMOL)] and diethyl azidocarboxylate (2.4 [ML,] 15.2 [MMOL).] The reaction was stirred at ambient temperature overnight. The reaction was concentrated in vacuo and chromatagraphed on silica gel to give the title compound (2.38 grams, 73 % [YIELD).,]

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; PFIZER PRODUCTS INC.; WO2004/9588; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 143557-91-9, category: amides-buliding-blocks

To a stirred solution of Intermediate 63 (0.68 g, 2.98 mmol) in dry DMF (10 mL) wasadded NaH (60 % dispersion in mineral oil,120 mg, 3.00 mmol). After the mixturewas stirred for 15 mm Intermediate 26 (0.5 g, 2.29 mmol) was added as one portion. The resulting mixture was stirred at RT for 48 h. The reaction mixture was poured onto brine and extracted into EtOAc. The organic layer was washed with brine, separated, dried over MgSO4, filtered and concentrated under reducedpressure to give brown oil. The crude material was purified by Biotage Isolera chromatography (silica gel, eluting with heptane-EtOAc, 1:0 to 0:1) to afford 531 mg (54% yield) of the title compound as an off-white powder.1H NMR (250 MHz, Chloroform-d): 6 [ppm] 7.71 (t, J = 1.4 Hz, 2H), 7.68 – 7.63 (m, 1H), 7.53 (d, J = 1.2 Hz, 1H), 7.13 (dd, J = 2.4, 1.3 Hz, 1H), 4.75 (tt, J = 10.6, 5.9Hz, 1H), 4.34 (5, 2H), 2.53 (d, J = 1.1 Hz, 3H), 2.20- 2.00 (m, 4H), 1.93 – 1.65 (m,4H), 1.49 (5, 9H).LCMS (Analytical Method A) Rt = 1 .46 mm, MS (ESIpos): m/z = 426.05 (M+H)+.

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Reference:
Patent; EVOTEC AG; DAVENPORT, Adam James; BRAEUER, Nico; FISCHER, Oliver Martin; ROTGERI, Andrea; ROTTMANN, Antje; NEAGOE, Ioana; NAGEL, Jens; GODINHO-COELHO, Anne-Marie; (703 pag.)WO2016/91776; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 143557-91-9, These common heterocyclic compound, 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, its 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.

[0178] A reaction flask was charged with crude compound 2 (5.5 g) in dry DMF (25 mL) under argon. NaH (60% in oil, 0.968 g, 24.2 mmol) was added in portions and the mixture was stirred at 50 C for 1 h. The mixture was cooled to rt and bromomethylcyclopropane (3.252 g, 24.2 mmol) was added followed by stirring at rt for 20 h under argon. The reaction mixture was quenched with water and the product extracted into ethyl acetate. The combined organic phases were dried over Na2S04, filtered, and concentrated. The product was purified by flash column chromatography (Si02; n-heptane/ethyl acetate 2: 1) to give the compound 3, 3a- cyclopropylmethoxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (3.354g). 1H NMR (CDCI3) delta 3.98 – 3.94 (m, 2H), 3.44 – 3.40 (m, 1H), 3.05 (d, 2H), 1.96 – 1.88 (m, 2H), 1.79 – 1.62 (m, 6H), 1.29 (s, 9H), 0.88 – 0.79 (m, 1H), 0.35 – 0.30 (m, 2H), 0.04 – 0.00 (m, 2H); 13C NMR (CDCI3) delta 153.4, 78.9, 73.0, 72.5, 52.7, 34.9, 28.5, 28.1, 10.9, 2.8.

Statistics shows that tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate is playing an increasingly important role. we look forward to future research findings about 143557-91-9.

Reference:
Patent; ACADIA PHARMACEUTICALS INC.; BURSTEIN, Ethan, S.; ESKILDSEN, Jorgen; OLSSON, Roger; LUHRS, Lauren, M.; WHEELER, Larry, A.; GIL, Daniel, W.; WO2014/152144; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics