Category: 2081-44-9

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

Example 95A (enantiomer 1)Step I: tetrahydro-2H-pyran-4-yl methanesulfonate; P At r.L to a solution of tetrahydro-4H-pyran-4-ol (90 uL, . mmol; Aldrich, Cat. No. 198234) in methylene chloride (3 mL) was added methanesulfonyl chloride (91 uL, 1.2 mmol), followed by triethylamine (0.20 mL, 1.5 mmol) and 4-dimethylaminopyridine (12 mg, 0.098 mmol). The mixture was stirred at r.L for 3 h. It was diluted with methylene chloride. The solution was washed with water and brine, dried over l^SCv After filtration, the filtrate was concentrated to yield 0.21 g of the product (crude) which was directly used in the next step reaction without further purification., 2081-44-9

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

Reference£º
Patent; INCYTE CORPORATION; ZHANG, Colin; QIAN, Ding-quan; ZHUO, Jincong; YAO, Wenqing; WO2010/75270; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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 (20 g ) in tetrahydrofuran (150 mL) and triethylamine (28.5 mL) is slowly added methanesulfonyl chloride (15.5 mL), while keeping the temperature below 30C. The mixture is stirred for 12 hours at room temperature. The precipitate is filtered off and washed twice with tetrahydrofuran. The combined organic phases are concentrated and partitioned between ethyl acetate and water. The organic phase is dried (Na2SO4) and concentrated to give the title compound. Yield: 29.4 g; TLC: rf = 0.36 (silicagel, petrole ether/ethyl acetate 1 :1 ); Mass spectrum (ESI+): m/z = 198 [M+NH4]+., 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; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; WO2013/144098; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

Step 2: Synthesis of Toluene-4-sulfonic acid tetrahydro-pyran-4-yl ester To a solution of 133 g (1.31 mol) of tetrahydro-pyran-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 room temperature and stirred for 18 h. The reaction is poured onto a stirred mixture of aqueous HCl/ice. The resulting precipitate is isolated by filtration and dissolved in DCM (1 L). The organic layer is washed with 1M aqueous HC1 solution (1 L), followed by saturated aqueous NaHC03 solution (1 L) and is then dried over Na2S04.Filtration and concentration of the filtrate under reduced pressure gives 300 g of toluene-4- sulfonic acid tetrahydro-pyran-4-yl ester as an orange oil. Yield: 90%, ES-MS: m/z: 257[M+H], 279 [M+Na]. 1H-NMR (250 MHz, CHLOROFORM-d) delta ppm 1.66 – 1.96 (4 H, m), 2.45 (3 H, s), 3.47 (2 H, ddd, 7=11.76, 8.19, 3.50 Hz), 3.79 – 3.95 (2 H, m), 4.69 (1 H, tt, 7=8.13, 4.13 Hz), 7.35 (2 H, d, 7=8.07 Hz), 7.76 – 7.87 (2 H, m)

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; BARTOLOZZI, Alessandra; BERRY, Angela; RIETHER, Doris; ERMANN, Monika; JENKINS, James Edward; MUSHI, Innocent; WO2011/88015; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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 an ice-cooled solution of oxan-4-ol (1.00 g, 9.79 mmol), Et3N (1.36 ml, 9.79 mmol) and catalytic amount DMAP in 20 ml of CH2Cl2 was added dropwise MsCl (0.76 ml, 9.79 mmol). The resulting mixture was stirred for 1 h and diluted with water. The mixture was extracted with CH2Cl2. The organic phase was washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The crude product was pure enough for use in the next step (1.65 g, 93.5 % yield).

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
Article; Zhang, Dengyou; Ai, Jing; Liang, Zhongjie; Li, Chunpu; Peng, Xia; Ji, Yinchun; Jiang, Hualiang; Geng, Meiyu; Luo, Cheng; Liu, Hong; Bioorganic and Medicinal Chemistry; vol. 20; 17; (2012); p. 5169 – 5180;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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.

Step A: Preparation of tetrahydro-2H-pyran-4-yl methanesulfonate: To a solution of tetrahydro-2H-pyran-4-ol (2.5 g, 24.5 mmol) in DCM (40 mL) was added DIEA (6.40 mL, 36.7 mmol) at 0 C and allowed to stir under nitrogen for 10 minutes. Methane sulfonyl chloride (2.18 mL, 28.1 mmol) was added slowly. The reaction was allowed to proceed for 1 hour at 0 C. The reaction was partitioned between 100 mL of DCM and 50 mL of 0.5 M hydrochloric acid. The layers were separated and the organic layer was then washed sequentially with water, saturated sodium bicarbonate, and brine. The organic layer was dried over MgSO t, filtered, and concentrated under reduced pressure and dried on high vacuum to afford tetrahydro-2H-pyran-4-yl methanesulfonate (4.4 g, 24.4 mmol, 99.7% yield).

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

Reference£º
Patent; ARRAY BIOPHARMA INC.; BOYS, Mark Laurence; BURGESS, Laurence, E.; GRONEBERG, Robert, D.; HARVEY, Darren, M.; HUANG, Lily; KERCHER, Timothy; KRASER, Christopher, F.; LAIRD, Ellen; TARLTON, Eugene; ZHAO, Qian; WO2011/130146; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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 (612 mg, 6 mmol) in DCM (5 mL) was added EtsN (1002 uL, 7.2 mmol) and MsCI (510 uL, 6.6 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours. After that the mixture wasconcentrated to give a white solid which was used for next step directly.

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

Reference£º
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; DENG, Wei; WO2014/86032; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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 mixture of NaH (1.8 g, 40 mmol) in anhydrous THF (10 mL) was added reagent 1 (2.0 g, 20 mmol). The mixture was stirred at room temperature for 1 h before addition of a solution of 4-methylbenzene-1 -sulfonyl chloride (4.6 g, 24 mmol) in THF (10 mL). The resulting mixture was stirred at room temperature for 15 h. The solution was quenched with saturated, aqueous NH4CI solution (30 mL). The mixture was extracted with EtOAc (100 mL x 3). The combined organic layers were dried over Na2S04 and evaporated to dryness. Flash chromatography (silica, petroleum ether : EtOAc 100:1 to 1 :1 ) gave reagent 2 (4.7 g, 92%). 1H NMR (CDCIs) delta 7.79 (d, J = 8.4 Hz, 2 H), 7.33 (d, J = 4.0 Hz, 2 H), 4.64-4.70 (m, 1 H), 3.82-3.87 (m, 2 H), 3.42-3.48 (m, 2 H), 2.43 (s, 3 H) , 1 .75-1.87 (m, 2 H), 1 .68-1.74 (m, 2 H)., 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; H. LUNDBECK A/S; ESKILDSEN, J¡ãrgen; WO2014/49133; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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.

2081-44-9, To a solution of tetrahydropyran-4-ol (1.0 g, 9.8 mmol) in DCM (5 mL) was added Et3N (triethylamine; 2.73 mL, 20 mmol). To the mixture was added a solution of methanesulfonyl chloride (0.91 mL, 12 mmol) in DCM (dichloromethane; 5 mL) at 0 C. The mixture was stirred at 0 C for 1 hour. Upon completion, the reaction mixture was treated with water (5 mL), and extracted with DCM (10 mL x 3). The organic layers were combined, washed with brine (10 mL x 3), dried over Na2S04, filtered and concentrated under reduced pressure to afford tetrahydropyran-4-yl methanesulfonate (1.3 g, crude) as a white solid, which was used directly in the next step.

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

Reference£º
Patent; SYROS PHARMACEUTICALS, INC.; ZHANG, Yi; AUSTGEN, Kathryn; CHUAQUI, Claudio Edmundo; MALOJCIC, Goran; SINKO, William; CIBLAT, Stephane; JAMES, Clint; GUAN, Huiping Amy; SAVOIE, Tracey Lodie; (179 pag.)WO2019/14513; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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.

General procedure: In the following Reaction Scheme A-2 Butyl 4-hydroxypiperidine-1-carboxylate (1 eq.) Or tetrahydro-2H-p yr-4-ol (1 eq.),Methanesulfonyl chloride (MsCl, 1 eq.),Triethylamine (Et3N, 1 eq.) And 4-dimethylaminopyridine (DMAP, 0.4 eq.) Were dissolved in dichloromethane at 0 C and stirred at room temperature for 12 hours.Water was added to the reaction solution at 0 C and extracted three times with dichloromethane.The combined organic solvent layers were dried with magnesium sulfate and concentrated.This was purified by column chromatography to obtain a compound substituted with methanesulfonate.Subsequently, 4-iodo-1H-pyrazole (1 eq.) Was dissolved in DMF, cooled to 0 C, 60% sodium hydride (NaH, 1.2 eq.) Was added to the solution and the mixture was stirred at room temperature for 1 hour.The previously obtained compound (1.1 eq) was added to the reaction solution, and the mixture was heated and stirred at 100 C.Water was added to the reaction solution at 0 C, extracted three times with ethyl acetate, and the combined organic solvent layer was dried over magnesium sulfate.The obtained organic solvent layer was concentrated and purified by column chromatography to obtain an intermediate.

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; Institute for Basic Science; KAIST; Hong Seung-u; Ma Sin-mi; Hong Sun-seon; Jeong Hoe-yun; (71 pag.)KR2019/23557; (2019); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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 (20 g ) in tetrahydrofuran (150 mL) and triethylamine (28.5 mL) is slowly added methanesulfonyl chloride (15.5 mL), while keeping the temperature below 30C. The mixture is stirred for 1 2 hours at room temperature. The precipitate is filtered off and washed twice with tetrahydrofuran. The combined organic phases are concentrated and partitioned between ethyl acetate and water. The organic phase is dried (Na2SO4) and concentrated to give the title compound. Yield: 29.4 g; TLC: rf = 0.36 (silicagel, petrole ether/ethyl acetate 1 :1 ); Mass spectrum (ESI+): m/z = 198 [M+NH4]+., 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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; WO2013/144097; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics