Category: 17366-48-2

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 17366-48-2, name is exo-8-Azabicyclo[3.2.1]octan-3-ol hydrochloride. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 17366-48-2

To a stirred solution of exo-8-azabicyclo[3.2.1]octan-3-ol hydrochloride (2.049 g, 12.52 mmol) and DIPEA (5.96 ml, 34.1 mmol) in DMF (15 ml) was added 5-bromo-2-chlorobenzenesulfonyl chloride (3.30 g, 11.38 mmol) at 0 C., the mixture was slowly rose to rt in 2 h and stirred at rt for 1 h. The solution was partitioned (EtOAc-brine). The organic layer was dried (Na2SO4), filtered and concentrated. The residue was used directly for next step. ESI-MS (M+H): 380.0, 382.0. To a mixture of the compound from Step 23a (4.3 g, 11.30 mmol) and imidazole (1.922 g, 28.2 mmol) in DMF (15 ml) was added TBSCl (2.043 g, 13.55 mmol) at 0 C. The resulting mixture was stirred overnight at rt. The solution was partitioned (EtOAc-brine). The organic layer was dried (Na2SO4), filtered and concentrated. The crude residue was chromatographed (silica, ethyl acetate/petroleum ether) to give the desired compound as a white solid (3.92 g, 70% over 2 steps). ESI-MS (M+H): 494.1, 496.1.H NMR (400 MHz, CDCl3) delta 8.21 (d, J=2.4 Hz, 1H), 7.55 (dd, J=8.4, 2.4 Hz, 1H), 7.35 (d, J=8.4 Hz, 1H), 4.27 (dd, J=4.7, 2.8 Hz, 2H), 3.95 (td, J=10.6, 5.4 Hz, 1H), 1.97 (dd, J=8.3, 4.3 Hz, 2H), 1.83 (ddd, J=13.2, 5.9, 3.1 Hz, 2H), 1.77-1.60 (m, 4H), 0.83 (s, 9H), 0.00 (s, 6H). To a stirred solution of the compound from Step 23b (1.00 g, 2.02 mmol) in THF (30.0 ml) was added a solution of 2.5 M n-BuLi (0.889 ml, 2.22 mmol) in hexanes at -78 C. and DMF (0.469 ml, 6.06 mmol). The resulting mixture was stirred at -78 C. for 30 minutes. The solution was partitioned (EtOAc-brine). The organic layer was dried (Na2SO4), filtered and concentrated. The crude residue was chromatographed (silica, ethyl acetate/petroleum ether) to give the desired compound as a white solid (250 mg, 28%). ESI-MS (M+H): 444.2, 446.2. To a stirred solution of the compound from Step 23c (340 mg, 0.766 mmol) in DMF (8.0 ml) was added trimethyl(trifluoromethyl)silane (654 mg, 4.60 mmol) at 0 C. The resulting mixture was warmed up slowly to rt and kept for 30 minutes. The solution was partitioned (EtOAc-brine). The organic layer was dried (Na2SO4), filtered and concentrated. The crude residue was taken into next step without further purification. ESI-MS (M+H): 586.1, 588.1.To a stirred solution of the compound from Step 23d (90 mg, 0.154 mmol) in MeOH (4.0 ml) was added K2CO3 (212 mg, 1.535 mmol) at 0 C. The resulting mixture was stirred at 0 C. for 1 h. The solution was partitioned (EtOAc-brine). The organic layer was dried (Na2SO4), filtered and concentrated. The crude residue was chromatographed (silica, ethyl acetate/petroleum ether) to give the desired compound as a white solid (62 mg, 79%). ESI-MS (M+H): 514.2, 516.2.To a stirred solution of the compound from Step 23e (50 mg, 0.097 mmol) in DCM (2 ml) was added Dess-Martin periodinane (61.9 mg, 0.146 mmol) at 0 C. . The resulting mixture was stirred at 0 C. for 1 h. The solution was partitioned between EtOAc and Na2S2O3 aqueous solution. The organic layer was dried (Na2SO4), filtered and concentrated. The crude residue was chromatographed (silica, ethyl acetate/petroleum ether) to give the desired compound as a white solid (40 mg, 80%). ESI-MS (M+H): 512.2, 514.2.To a stirred solution of the compound from Step 23f (15 mg, 0.029 mmol) and 3,4,5-trifluoroaniline (10.77 mg, 0.073 mmol) in toluene (1 mL) was added titanium(IV) isopropoxide (0.051 ml, 0.176 mmol). The resulting mixture was stirred at reflux (120 C.) for 15 h. The mixture was cooled to rt. Then sodium triacetoxyborohydride (18.63 mg, 0.088 mmol) was added. The mixture was stirred at rt for 1 h. The solution was partitioned (EtOAc-brine). The organic layer was dried (Na2SO4), filtered and concentrated. The crude residue was chromatographed (silica, ethyl acetate/petroleum ether) to give the desired compound as a white solid (5 mg, 27%). ESI-MS (M+H): 643.2, 645.2.To a stirred solution of the compound from Step 23g (6 mg, 9.3 mumol) in MeOH (1.0 ml) was added a solution of 4N HCl (0.12 ml, 0.47 mmol) at 0 C. The resulting mixture was stirred at 0 C. for 45 minutes. The solution was partitioned (EtOAc-brine). The organic layer was dried (Na2SO4), filtered and concentrated. The crude residue was chromatographed (silica, MeOH/DCM) to give the title compound as a white solid (4 mg, 81%). ESI-MS (M+H): =529.1, 531.1.1H NMR (400 MHz, MeOH-d4) delta 8.30 (d, J=2.2 Hz, 1H), 7.78 (dd, J=8.3, 2.2 Hz, 1H), 7.68 (d, J=8.2 Hz, 1H), 6.62-6.39 (m, 2H), 5.50 (q, J=7.5 Hz, 1H), 4.33-4.16 (m, 2H), 3.98 (dt, J=10.8, 5.1 Hz, 1H), 2.02-1.86 (m, 2H), 1.84-1.55 (m, 6H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 17366-48-2, exo-8-Azabicyclo[3.2.1]octan-3-ol hydrochloride.

Reference:
Patent; Enanta Pharmaceuticals, Inc.; Or, Yat Sun; Jin, Meizhong; Kass, Jorden; Cao, Hui; Gao, Xuri; Li, Wei; Peng, Xiaowen; Qiu, Yao-Ling; (43 pag.)US2017/217974; (2017); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 17366-48-2, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 17366-48-2 as follows.

1-(Diphenylmethyl)azetidin-3-one (see Bioorg. Med. Chem. Lett.; 13; 2003; 2191-2194, 2.12 g, 9.0 mmol) was dissolved in methylene chloride (25 mL) and the resultant solution was added to a slurry of exo-8-azabicyclo[3.2.1]octan-3-ol hydrochloride (norpseudotropine hydrochloride) (see U.S. Pat. No. 6,699,870, 2.12 g, 9.0 mmol) in methylene chloride (25 mL). Another portion of methylene chloride (20 mL) was added and then DIPEA (3.47 g, 26.8 mmol), acetic acid (1.09 g, 18.2 mmol) and sodium triacetoxyborohydride (3.79 g, 17.9 mmol) were added in the given order. The mixture was stirred at RT for 4 days and then diluted with methylene chloride (150 mL). The solution was washed with a mixture of aqueous Na2CO3 (sat. 20 mL) and aqueous NaHCO3 (sat. 15 mL) and then washed with aqueous NaHCO3 (sat. 15 mL). The organic solution was dried (Na2SO4) and then the solvent was removed by evaporation. The product was purified twice by column chromatography on silica gel first eluting with methylene chloride/methanol (95/5) and then with methylene chloride/ammonia saturated methanol (9/1). There was obtained 1.9 g (60%) of exo-8-[1-(diphenylmethyl)azetidin-3-yl]-8-azabicyclo[3.2.1]octan-3-ol as a white foam. 1H NMR (400 MHz, CDCl3). 1.4-1.6 (m, 4H), 1.7-2.0 (m, 4H), 2.8-2.9 (b, 2H), 3.1 (b, 2H), 3.3-3.5 (m, 3H), 3.8-3.9 (m, 1H), 4.4-4.5 (s, 1H), 7.2 (m, 2H), 7.3 (m, 4H), 7.4 (m, 4H); LCMS: m/z 349 (M+1)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17366-48-2, its application will become more common.

Reference:
Patent; Antonsson, Thomas; US2008/146538; (2008); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 17366-48-2 ,Some common heterocyclic compound, 17366-48-2, molecular formula is C7H14ClNO, 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.

General procedure: General Method F (copper catalyzed amination of aryl-hal) A microwave vial was charged with 1 ,4-diiodobenzene or l-bromo-4-iodobenzene (1.0 equiv), Cul (20 mol%), BINOL (20 mol%), and K3P04 (2 equiv.). The vial was capped and then evacuated and backfilled with Ar. Dialklyamine (1.2 equiv) and DMF were then added. The resulting mixture was stirred at rt for 2 to 4 d. The mixture was diluted with EtOAc, filtered through a cake of Celite and the filtrate was concentrated to give the crude product. Crude product was purified by flash chromatography to give the title compound.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 17366-48-2, exo-8-Azabicyclo[3.2.1]octan-3-ol hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; LIU, Yong; LANG, Yunhui; NG, Grace; LI, Sze-Wan; PAULS, Heinz W.; LAUFER, Radoslaw; PATEL, Narendra Kumar B.; SAMPSON, Peter Brent; FEHER, Miklos; AWREY, Donald E.; WO2014/56083; (2014); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 17366-48-2 , The common heterocyclic compound, 17366-48-2, name is exo-8-Azabicyclo[3.2.1]octan-3-ol hydrochloride, molecular formula is C7H14ClNO, 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.

8-Aza-bicyclo [3.2. 1] octanol hydrochloride (5.1 g, 31.45 mmol)) and sodium carbonate (13.3 g, 125.8 mmol) are suspended in 150 mi of ethanol at room temperature. 2-Bromo- ethanol (4.4 ml, 62.9 mmol) is added dropwise within 20 minutes and the reaction mixture is refluxed for 15 hours. After cooling to room temperature the reaction mixture is evaporated under reduced pressure. The mixture is stirred with 200 ml of DCM and filtered. The clear filtrate is dried over anhydrous sodium sulfate, filtered, evaporated under reduced pressure und dried at high vacuum. Yield : 5.4 g (100%) of a colorless oil. MS (ESI) : 172 [M+H] +, 1 H-NMR (DMSO-d6) : 5 (ppm) 4.25 (d, 2H), 3.78 (t, 1H), 3.42 (t, 2H), 3.06 (m, 2H), 2.36 (t, 2H), 2.03 (m, 2H), 1.85 (m, 2H), 1.75 (m, 2H), 1. 55 (d, 2H).

The synthetic route of 17366-48-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GmbH; WO2005/77932; (2005); A2;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts