New learning discoveries about 2081-44-9

2081-44-9, The synthetic route of 2081-44-9 has been constantly updated, and we look forward to future research findings.

2081-44-9, Tetrahydro-2H-pyran-4-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of 1-(2,6-dichloro-3-fluorophenyl)ethan-1-one 11 (20.00 g, 96.60 mmol) in 100 mL of MeOH was added portionwise NaBH4 (7.31 g, 193.21 mmol). The resulting mixture was stirred at room temperature for 2 h and then quenched with 20 mL of water. After the removal of MeOH under vacuum, the residue was extracted with EA and washed with brine. The organic layer was dried over anhydrous Na2SO4 and concentrated under vacuum to afford 1-(2,6-dichloro-3-fluorophenyl)ethan-1-ol, which was pure enough for use in the next step. 1H NMR (400 MHz, CDCl3) delta 7.26 (dd, J = 4.8, 8.8 Hz, 1H), 7.02 (dd, J = 8.0, 8.8 Hz, 1H), 5.57 (q, J = 6.8 Hz, 1H), 2.86 (br, 1H), 1.64 (d, J = 6.8 Hz, 3H). To a solution of 1-(2,6-dichloro-3-fluorophenyl)ethan-1-ol (19.00 g, 90.89 mmol) in 150 mL of CH2Cl2 was added Et3N (13.27 mL, 95.43 mmol) and catalytic amount of DMAP. The resulting solution was cooled in an ice bath and added dropwise MsCl (7.39 mL, 95.43 mmol). After complete addition of MsCl, the reaction mixture was maintained in the ice bath for 1 h and then 30 mL of water was added to the reaction mixture. The organic phase was washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum to afford 1-(2,6-dichloro-3-fluorophenyl)ethyl methanesulfonate (12), which was pure enough for use in the next step. Yield: 84%.

2081-44-9, The synthetic route of 2081-44-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Zhang, Dengyou; Zhang, Xiaowei; Ai, Jing; Zhai, Yun; Liang, Zhongjie; Wang, Ying; Chen, Yi; Li, Chunpu; Zhao, Fei; Jiang, Hualiang; Geng, Meiyu; Luo, Cheng; Liu, Hong; Bioorganic and Medicinal Chemistry; vol. 21; 21; (2013); p. 6804 – 6820;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Downstream synthetic route of 2081-44-9

2081-44-9, As the paragraph descriping shows that 2081-44-9 is playing an increasingly important role.

2081-44-9, Tetrahydro-2H-pyran-4-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Synthesis of compound 97.2. [00609] A solution of oxan-4-ol, compound 97.1 (7.0 g, 68.54 mmol, 1.00 equiv) in dichloromethane (100 mL) was added triphenylphosphine (27.0 g, 102.94 mmol, 1.50 equiv) and imidazole (7.0 g, 102.82 mmol, 1.50 equiv) at room temperature. This was followed by addition of iodine (18.3 g, 72.05 mmol, 1.05 equiv) in several batches at 0C. The resulting solution was stirred for 2 h at room temperature under nitrogen. After completion, the reaction was quenched with 5% HC1 solution, extracted with dichloromethane (100 mL x 3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. Crude was purified via flash column chromatography to afford 9.6 g of 4-iodooxane, compound 97.2 as colorless oil.

2081-44-9, As the paragraph descriping shows that 2081-44-9 is playing an increasingly important role.

Reference£º
Patent; NIMBUS IRIS, INC.; CHAUDHARY, Divya; KAPELLER-LIBERMANN, Rosana; WO2014/194242; (2014); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Downstream synthetic route of 2081-44-9

The synthetic route of 2081-44-9 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2081-44-9,Tetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

A solution of tetrahydro-2H-pyran-4-ol (25.0 g, 245 mmol), TEA (51 mL, 367 mmol) and trimethylamine hydrochloride (2.34 g, 24.5 mmol) were stirred in DCM (750 mL) at RT for 10 minutes and cooled to 0C. 4-Methylbenzenesulfonyl chloride (51.3 g, 269 mmol) was added and the mixture stirred at RT for 17h. The mixturewas treated with N,N-dimethylethane-1,2-diamine (31.6 mL, 294 mmol) and water. The aqueous layer was extracted three times with DCM. The combined organic portions were concentrated under reduced pressure and purified via column chromatography (silica gel, hexane/ EE gradient) to give 58.5 g (93% yield) of the title compound.1H NMR (400 MHz, DMSO-d6) 6 [ppm] 1.51 – 1.61 (m, 2 H) 1.74 (dq, J=13.04, 3.65 Hz, 2 H) 2.42 (5, 3 H) 3.39 (ddd, J=11.75, 8.97, 3.03 Hz, 2 H) 3.71 (dt, J=11.81,4.71 Hz, 2 H) 4.69 (tt, J=8.65, 4.23 Hz, 1 H) 7.47 (d, J=8.08 Hz, 2 H) 7.81 (d, J=8.34 Hz, 2 H)., 2081-44-9

The synthetic route of 2081-44-9 has been constantly updated, and we look forward to future research findings.

Reference£º
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;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Downstream synthetic route of 2081-44-9

The synthetic route of 2081-44-9 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2081-44-9,Tetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

EXAMPLE 14 1-[2,4-DICHLORO-5-(TETRAHYDRO-4H-PYRAN-4-YLOXY)PHENYL]-3-METHYL-4-DIFLUOROMETHYL-Delta2 -1,2,4-TRIAZOLIN-5-ONE To a chilled solution of 1.0 g (0.0098 mole) of tetrahydro-4H-pyran-4-ol in 10 mL of pyridine was added 1.91 g (0.01 mole) of 4-methylphenylsulfonyl chloride over 3-5 minutes. The reaction mixture was stirred at about -4 C. for 15 minutes, then was allowed to stand with cooling for 16 hours. The reaction mixture was mixed with ice-water, and the solid product, tetrahydro-4H-pyran-4-yl 4-methylphenylsulfonate, collected on a filter paper, wgt. 1.6 g, mp 56-57 C., 2081-44-9

The synthetic route of 2081-44-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; FMC Corporation; US4702763; (1987); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Brief introduction of 2081-44-9

2081-44-9, 2081-44-9 Tetrahydro-2H-pyran-4-ol 74956, aTetrahydropyrans compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2081-44-9,Tetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

A flask was charged with 4-hydroxytetrahydropyran (3.00 g, 29.4 mmol), Methanesulfonyl chloride (2.39mL, 30.9 mmol), triethylamine (8.20 mL, 58.8 mmol), and CH2Cl2. The resulting mixture was stirred overnight at room temperature. The reaction mixture was then washed with saturated aqueous NaHCO3 (100 mL) and water (100 mL), dried over Na2SO4, filtered and concentrated under reducedpressure. The crude product thus obtained was used without further purification.

2081-44-9, 2081-44-9 Tetrahydro-2H-pyran-4-ol 74956, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; ChemoCentryx, Inc.; Fan, Junfa; Krasinski, Antoni; Lange, Christopher W.; Lui, Rebecca M.; McMahon, Jeffrey P.; Powers, Jay P.; Zeng, Yibin; Zhang, Penglie; US2014/154179; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Brief introduction of 2081-44-9

2081-44-9, 2081-44-9 Tetrahydro-2H-pyran-4-ol 74956, aTetrahydropyrans compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2081-44-9,Tetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

To a solution of tetrahydro-2H-pyran-4-ol (4 mL, 41.11 mmol) in DCM (60 mL) was added TEA (9 mL, 63.9 mmol) at 0. After stirring 5 min, methanesulfonyl chloride (3.5 mL, 45 mmol) was added slowly to the mixture. The resulting mixture was stirred for 1 h and warmed to rt, and then further stirred overnight. The reaction mixture was diluted with water (50 mL) . The resulting mixture was extracted with DCM (100 mL ¡Á 3) . The combined organic layers were dried over anhydrous Na2SO4and concentrated in vacuo to give a light yellow solid product (7 g, 94.5) .[1586]MS (ESI, pos. ion) m/z: no response.

2081-44-9, 2081-44-9 Tetrahydro-2H-pyran-4-ol 74956, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Bing; ZHANG, Yingjun; CHENG, Changchung; HUANG, Jiuzhong; BAI, Shun; REN, Xingye; LI, Zhi; ZHOU, Youbai; (368 pag.)WO2016/615; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Simple exploration of 2081-44-9

As the paragraph descriping shows that 2081-44-9 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2081-44-9,Tetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

To 133 g (1.31 mol) of tetrahydropyran-4-ol in pyridine (1.5 L) are added 373 g (1.95 mol) of p-toluenesulfonylchloride portionwise at 10 C. After complete addition the reaction is allowed to warm to RT and stirred for 18 h. The reaction is poured onto a stirred mixture of aq. HCl/ice. The resulting precipitate is isolated by filtration and dissolved in DCM (1 L). The organic layer is washed with 1 M aq. HCl solution (1 L), followed by sat. aq. NaHCO3 solution (1 L) and is then dried over Na2SO4. Filtration and concentration of the filtrate under reduced pressure gives 300 g of toluene-4-sulfonic acid tetrahydropyran-4-yl ester. Yield: 90%; ESI-MS: 257 [M+H]+, 2081-44-9

As the paragraph descriping shows that 2081-44-9 is playing an increasingly important role.

Reference£º
Patent; Boehringer Ingelheim International GmbH; Riether, Doris; Binder, Florian Paul Christian; Doods, Henri; Mueller, Stephan Georg; Nicholson, Janet Rachel; Sauer, Achim; US8865744; (2014); B1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Some tips on 2081-44-9

As the paragraph descriping shows that 2081-44-9 is playing an increasingly important role.

2081-44-9, Tetrahydro-2H-pyran-4-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of tetrahydro-2H-pyran-4-ol (4.5 g, 44 mmol) in DCM (200 mL) was added TEA (5.4 g, 53.5 mmol) and MeSO2C1 (3.73 mL, 50 mmol) at ice-bath temperature. The reaction mixture was stirred at rt for 16 h. The reaction was quenched with water and the organic layer was washed with brine, dried and concentrated to give 7.9 g of the title compound (100%). ?H NMR (400 MHz, CDC13): oe 1.84-1.93 (2H, m), 2.03-2.08 (2H, m), 3.05 (3H, s), 3.52-3.58 (2H, m), 3.92-3.97 (2H, m), 4.87-4.94 (1H, m)., 2081-44-9

As the paragraph descriping shows that 2081-44-9 is playing an increasingly important role.

Reference£º
Patent; QUANTICEL PHARMACEUTICALS, INC.; KANOUNI, Toufike; STAFFORD, Jeffrey, Alan; VEAL, James, Marvin; WALLACE, Michael, Brennan; WO2014/151106; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Downstream synthetic route of 2081-44-9

2081-44-9, The synthetic route of 2081-44-9 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2081-44-9,Tetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

To a solution of tetrahydro-2H-pyran-4-ol (500 mg, 4.90 mmol) in DCM (16 mL) was added TEA (0.882 mL, 6.36 mmol) followed by MsCl (0.458 mL, 5.87 mmol) at 0 C. The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with DCM, washed with water, 2 N aq. HCl, saturated aq. NaHCO3, and brine successively, dried over Na2SO4, filtered and concentrated in vacuo to afford tetrahydro-2H-pyran-4-yl methanesulfonate (882 mg, 100%) as a colorless oil, which was used for the next reaction without further purification. 1H-NMR (CDCl3, Varian, 400 MHz): delta 1.84-1.92 (2H, m), 2.03-2.07 (2H, m), 3.04 (3H, s), 3.52-3.58 (2H, m), 3.92-3.97 (2H, m), 4.87-4.93 (1H, m).

2081-44-9, The synthetic route of 2081-44-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; HANDOK INC.; CMG Pharmaceutical Co., Ltd.; Kim, Moonsoo; Lee, Chaewoon; Lee, Gilnam; Yoon, Cheolhwan; Seo, Jeongbeob; Kim, Jay Hak; Lee, Minwoo; Jeong, Hankyul; Choi, Hyang; Jung, Myung Eun; Lee, Ki Nam; Kim, Hyun Jung; Kim, Hye Kyoung; Lee, Jae Il; Lee, MinWoo; Kim, Misoon; Choi, Soongyu; (124 pag.)US2016/168156; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

New learning discoveries about 2081-44-9

2081-44-9, As the paragraph descriping shows that 2081-44-9 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2081-44-9,Tetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

A RBF was charged with tetrahydro-2H-pyran-4-ol (2.0 g, 19.58 mmol), imidazole (1.600 g, 23.50 mmol), triphenylphosphine (5.39 g, 20.56 mmol), and tetrahydrofuran (39.2 ml) and cooled to 0 C. A solution of iodine (5.96 g, 23.50 mmol) in tetrahydrofuran (39.2 ml) was added slowly dropwise. The reaction was warmed to room temperature and stirred overnight. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (RediSep Gold 80 g, gradient elution 0-50% EtOAc:Heptane) to afford 4-iodotetrahydro-2H-pyran (2.67 g, 12.59 mmol, 64.3% yield) as a clear light yellow oil.

2081-44-9, As the paragraph descriping shows that 2081-44-9 is playing an increasingly important role.

Reference£º
Patent; Amgen Inc.; Weiss, Matthew; Boezio, Alessandro; Boezio, Christiane; Butler, John R.; Chu-Moyer, Margaret Yuhua; Dimauro, Erin F.; Dineen, Thomas; Graceffa, Russell; Guzman-Perez, Angel; Huang, Hongbing; Kreiman, Charles; La, Daniel; Marx, Isaac E.; Milgrim, Benjamin Charles; Nguyen, Hanh Nho; Peterson, Emily; Romero, Karina; Sparling, Brian; US9212182; (2015); B2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics