Category: 137052-08-5

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.137052-08-5,1-(Tetrahydro-2H-pyran-4-yl)ethanone,as a common compound, the synthetic route is as follows.

KHMDS (1M in THF) (39.0 mL, 39.0 mmol) was added to THF (150 mL) at -78C under nitrogen. A solution of 1-(tetrahydro-2H-pyran-4-yl)ethanone (5 g, 39.0 mmol) in THF (20 mL) was added and the mixture was stirred at -78C under nitrogen for 1 .5h, giving a pale yellow solution. A solution of N-(5- chloropyridin-2-yl)-1 ,1 ,1 -trifluoro-N-((trifluoromethyl)sulfonyl)methanesulfonamide (15.32 g, 39.0 mmol) in THF (25 mL) was added over 20 minutes and the resulting orange, then colourless mixture was allowed to warm slowly to room temperature and stirred overnight. The reaction was quenched with NaHCO3 and the crude product extracted with MTBE (300 mL). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated under vacuum. The residue was dissolved in a small amount of 10% EtOAc:lsohexane and loaded on a 40g column. The crude product was purified by chromatography (Si02, 40 g column, 0-10% EtOAc/isohexane). Fractions containing product were combined, filtered, washing with 10% EtOAc:lsohexane, then concentrated. A solid formed in the residue, which was then taken up in 10% EtOAc:lsohexane, filtered through cotton wool. The filtrate was then loaded on a 40g column and the crude product was purified by chromatography (Si02, 40 g column, 0-10% EtOAc/isohexane) to afford 1 -(tetrahydro-2H-pyran-4-yl)vinyl trifluoromethanesu Ifonate (6.17 g, 20.15 mmol, 51.7% yield) as a colourless oil. 1H NMR (CDCI3) O: 5.14 (dd, 1H), 4.94 (dd, 1H), 4.06 – 3.98 (m, 2H), 3.41 (td, 2H), 2.54 -2.41 (m, 1 H), 1.89 – 1.79 (m, 2H), 1.66 – 1.50 (m, 2H)., 137052-08-5

The synthetic route of 137052-08-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASTEX THERAPEUTICS LIMITED; CANCER RESEARCH TECHNOLOGY LIMITED; HOWARD, Steven; CONS, Benjamin, David; ST. DENIS, Jeffrey, David; GRIFFITHS-JONES, Charlotte, Mary; HISCOCK, Steven, Douglas; HOLVEY, Rhian, Sara; BURNS, Alan, Richard; COUSIN, David; DEXTER, Hannah, Louise; PARRA, Guillaume, Francois; WATTS, John, Paul; JEWELL, Robert; STOCKWELL, Jennifer, Ann; HIRST, Kim, Louise; LEMASSON, Isabelle, Anne; NASH, David, John; OSBORNE, James, Daniel; PRIEDE, Jonas, Calleja; RICHARDS, Nicholas, Paul; DUMAS, Aaron, Michael; BISHOP, Brian, Christopher; PARRY-JONES, David; SCOTT, Jeremy, Peter; SHAUNMUGHAM, Meenakshi, Sundaram; MULLENS, Peter, Richard; LATHBURY, David, Charles; DIXON, Darren, James; GAUNT, Matthew, James; (291 pag.)WO2018/178691; (2018); 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.137052-08-5,1-(Tetrahydro-2H-pyran-4-yl)ethanone,as a common compound, the synthetic route is as follows.

To a solution of 4-bromo- 1 -chloro-2-(3-methoxypropoxy)bcnzcne (27.9 g, 0. 1 mo I ) in THF (300 ml.) was added l -tetrahydropyran-4-ylethanone (25 g, 0.2 mol), Pd2(dba)3 ( 1 .37 g, 1.5 mmol ), Xantphos ( 1 .74 g, 3.0 mmol) and sodium rm-butoxidc (28 g, 0.3 mol ). The result ing mixture was st irred for 8 h at 60 C under argon atmosphere. After being cooled to rt, the result ing suspension was filtered with suct ion. The filter cake was poured into water and acidified to pH=3 ith 2 M hydrochloride acid. The mixture was extracted with ethyl acetate (400 ml. ) 2 times and the combined organic layers were washed with water ( 200 ml. ) and brine, dried over anhydrous Na2S04 and concentrated to give 2-[4-chloro-3-(3- methoxypropoxy)phenyi ]- l -tetrahydropyran-4-yl-ethaiione (30 g) as a ye 1 low oil.To a solution of 4-bromo- 1 -chloro-2-(3-methoxypropoxy)bcnzcne (27.9 g, 0. 1 mo I ) in THF (300 ml.) was added l -tetrahydropyran-4-ylethanone (25 g, 0.2 mol), Pd2(dba)3 ( 1 .37 g, 1.5 mmol ), Xantphos ( 1 .74 g, 3.0 mmol) and sodium rm-butoxidc (28 g, 0.3 mol ). The result ing mixture was st irred for 8 h at 60 C under argon atmosphere. After being cooled to rt, the result ing suspension was filtered with suct ion. The filter cake was poured into water and acidified to pH=3 ith 2 M hydrochloride acid. The mixture was extracted with ethyl acetate (400 ml. ) 2 times and the combined organic layers were washed with water ( 200 ml. ) and brine, dried over anhydrous Na2S04 and concentrated to give 2-[4-chloro-3-(3- methoxypropoxy)phenyi ]- l -tetrahydropyran-4-yl-ethaiione (30 g) as a ye 1 low oil.

137052-08-5, The synthetic route of 137052-08-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HAN, Xingchun; JIANG, Min; WANG, Jianhua; ZHOU, Chengang; WANG, Yongguang; YANG, Song; (135 pag.)WO2016/71215; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

137052-08-5, 1-(Tetrahydro-2H-pyran-4-yl)ethanone is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a 100-mL round-bottom flask was placed a solution of 1-(tetrahydro-2H-pyran-4-yl)ethan-1-one (10 g,78.0 mmol) in THF (200 mL) then the solution was cooled to 0C and NaBH4 (1.50 g,39.5 mmol) was added. The reaction was stirred for 30 mm at 0C,quenched by the addition of water,and extracted withEtOAc. The organic extracts were combined and concentrated under reduced pressure affording 10 g (98%) of the title compound as colorless oil. Mass Spectrum (LCMS,ESI pos):Calcd. for C7H15O2: 131.1 (M+H); Found: 131.2.

137052-08-5, 137052-08-5 1-(Tetrahydro-2H-pyran-4-yl)ethanone 9877365, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; PROTEOSTASIS THERAPEUTICS, INC.; MUNOZ, Benito; BASTOS, Cecilia, M.; PARKS, Daniel; KOMBO, David; (301 pag.)WO2017/62581; (2017); 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.137052-08-5,1-(Tetrahydro-2H-pyran-4-yl)ethanone,as a common compound, the synthetic route is as follows.

137052-08-5, Under nitrogen protection,(R) -MeCBS (718.3 mL, 1 M solution in toluene) was added to a solution of borane dimethyl sulfide (718.3 mL, 7.183 mol) in tetrahydrofuran (4.6 L) at -10 to 0 C.Maintain low temperature conditions,Compound 15 (920 g, 7.183 mol) was added dropwise to the reaction system.After completion of the dropwise addition,The reaction system was stirred at 0 to 5 C for 10 minutes.(2N, 4L) was added slowly at -5 to 0 C to quench the reaction,After stirring for 6 hours, sodium chloride was added until saturation,Methyl tert-butyl ether (2 L) was added and stirred for 5 minutes,The filter cake was rinsed with methyl tert-butyl ether (2 L).The filtrate was allowed to stand,The aqueous phase was extracted with methyl tert-butyl ether until the desired product was not detected in the aqueous phase.The organic phases were combined,And washed with saturated brine (5 L)Dried over anhydrous sodium sulfate,Concentration by filtration afforded crude compound 16 (846 g) as a pale yellow oil,Without further purification,Can be directly used for the next reaction,e.e. value of the compound 16 of Example 10 derived by the reaction was carried out by.

As the paragraph descriping shows that 137052-08-5 is playing an increasingly important role.

Reference£º
Patent; Medchemexpress China Co., Ltd.; Wang, Guangyong; Li, Chaoping; Zhou, Zhiguo; Gao, Qiang; Zheng, Baofu; (12 pag.)CN105669647; (2016); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

137052-08-5, 1-(Tetrahydro-2H-pyran-4-yl)ethanone is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 179: N-(4-methoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)ethanamine To a stirred solution of 1-(tetrahydro-2H-pyran-4-yl)ethanone (3.2 g, 24.97 mmol) in DCM) (50 mL was added (4-methoxyphenyl)methanamine (6.87 g, 50.1 mmol). The resulting yellow solution was stirred for 4.5 h and sodium triacetoxyborohydride (10 g, 48.6 mmol) added. The white suspension was stirred. The reaction mixture was partitioned between DCM and aq. sat. NaHCO3. The organic layer was removed and the aqueous extracted 3 times with DCM. The combined organic phases were passed through a hydrophobic frit and concentrated in vacuo to give a yellow oil. The oil was dissolved in DCM, purified by silica gel chromatography eluting with EtOAc:EtOH (7.5 – 25%) and evaporated in vacuo to give the title compound as a yellow oil. The total yield of the reaction was 80%. LCMS (System A): tRET = 1.27 min, MH+ = 366.

137052-08-5, The synthetic route of 137052-08-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BIT, Rino Antonio; BROWN, John Alexander; HUMPHREYS, Philip G.; JONES, Katherine Louise; (240 pag.)WO2016/146738; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

137052-08-5, 1-(Tetrahydro-2H-pyran-4-yl)ethanone is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

First add 1- (tetrahydro-2H-pyran-4-yl) ethanone (10g, 78.02mmol) to 50mL of methanol,After cooling to -10 C, liquid bromine (4.0 mL, 78.02 mmol) was added to the reaction under an argon atmosphere.It was then reacted at 0 C for 45 min, followed by 10 C for 45 min.Sulfuric acid (27.5mL, 11M) was added to the above system, returned to room temperature and stirred overnight.After the reaction was completed, saturated brine and ethyl acetate were added for extraction, and the organic phases were combined, washed sequentially with saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title product.

137052-08-5, The synthetic route of 137052-08-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Nanjing Shenghe Pharmaceutical Co., Ltd.; Wang Yong; Zhao Liwen; Wang Yazhou; Zhang Yan; Wang Xiaowei; Wang Hai; Guo Zhuang; Lv Kunzhi; Chang Yujie; Chen Hongyan; Xu Guofeng; (37 pag.)CN111072645; (2020); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

137052-08-5, 1-(Tetrahydro-2H-pyran-4-yl)ethanone is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Combine selenium dioxide (181.80 g, 1.64 mol), 1,4-dioxane (630 mL), acetic acid (31.5 mL, 0.67 eq), and water (31.5 mL). Heat to 90 C and add 1-(tetrahydro-pyran-4-yl)-ethanone (105.0 g, 1.0 eq) dropwise. Stir at 90 C overnight. After cooling, filter through a plug of silica/Celite and wash with tetrahydrofuran (2.5 L). Dry the organics over anhydrous magnesium sulfate, filter, and concentrate in vacuo. Dissolve the crude material in methanol (500 mL) and add to a solution of tert-butyl 4-formylpiperidine-1-carboxylate (174.72 g, 1.0 eq) and ammonium acetate (315.74 g, 5.0 eq) in methanol (1.45 L) at 0 C. Stir overnight. Filter through silica/Celite and wash with ethyl acetate and methanol. Concentrate the filtrate in vacuo. Dilute with methyl tert-butyl ether (400 mL) and water (400 mL), then adjust the pH to 2 by addition of aqueous 85% phosphoric acid. Separate the layers and wash the aqueous phase with methyl tert-butyl ether (200 mL). Basify the resulting aqueous phase with solid sodium carbonate to pH 10 and extract with ethyl acetate (3 x 200 mL). Wash the organics with saturated aqueous sodium chloride. Dry the organics over anhydrous magnesium sulfate, filter, and concentrate in vacuo to afford title compound 19c, tert-butyl 4-(4-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-2-yl)piperidine-1-carboxylate (105.1 g, 38%). MS (ES) m/z = 336 [M]+, 1H NMR (300.16 MHz, CDCl3): 6.63 (s, 1H), 4.26-4.11 (m, 2H), 4.07-4.00 (m, 2H), 3.51 (td, J=11.7, 1.8 Hz, 2H), 2.95-2.73 (m, 2H), 2.05-1.87 (m, 3H), 1.79-1.61 (m, 3H), 1.61-1.51 (m, 4H), 1.46 (s, 9H).

137052-08-5, As the paragraph descriping shows that 137052-08-5 is playing an increasingly important role.

Reference£º
Article; Parthasarathy, Saravanan; Henry, Kenneth; Pei, Huaxing; Clayton, Josh; Rempala, Mark; Johns, Deidre; De Frutos, Oscar; Garcia, Pablo; Mateos, Carlos; Pleite, Sehila; Wang, Yong; Stout, Stephanie; Condon, Bradley; Ashok, Sheela; Lu, Zhohai; Ehlhardt, William; Raub, Tom; Lai, Mei; Geeganage, Sandaruwan; Burkholder, Timothy P.; Bioorganic and Medicinal Chemistry Letters; vol. 28; 10; (2018); p. 1887 – 1891;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

137052-08-5, 1-(Tetrahydro-2H-pyran-4-yl)ethanone is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

NaH (60% dispersion in mineral oil) (0.340 g; 8.5 mmol) was added to a solution of dimethyl carbonate (0.83 mL; 9.85 mmol) in 1,4-dioxane (4.00 mL) (1847) The mixture was heated at 90 C and l-(tetrahydro-2H-pyran-4-yl) ethanone (0.5 g; 3.90 mmol) in 1,4-dioxane (1.00 mL) was added to the suspension. The reaction mixture was stirred at reflux for 3 hours. Water was added and few drops of an aqueous solution of 3N HC1. (1848) The mixture was extracted twice with ethylic ether. The organic layer was decanted and the solvent was evaporated until dryness to give 0.65 g of intermediate 754 (89%).

137052-08-5, The synthetic route of 137052-08-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier, Alexis, Georges; LIGNY, Yannick, Aime, Eddy; GROSS, Gerhard, Max; JACOBY, Edgar; MEERPOEL, Lieven; GREEN, Simon, Richard; HYND, George; KULAGOWSKI, Janusz, Jozef; MACLEOD, Calum; MANN, Samuel, Edward; (472 pag.)WO2018/2217; (2018); 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.137052-08-5,1-(Tetrahydro-2H-pyran-4-yl)ethanone,as a common compound, the synthetic route is as follows.

(i?)-2-Methylpropanesulfinamide (106.9 g, 882.0 mmol) and titanium tetraethoxide (201.6 g, 883.6 mmol) were added to a solution of 4-acetyltetrahydropyran (112.5 g, 877.7 mmol) in THF (1.4 L) under an inert atmosphere and the mixture heated to reflux for 18 h. The mixture was allowed to cool and poured in to brine (850 mL). The resulting slurry was diluted with EtOAc (1 L) and the mixture filtered through celite. The resulting two phases were separated. The filter cake was washed with EtOAc (4 x 1 L) and the combined organics dried (Na2S04), filtered and concentrated under vacuum (40-45C) to give a cloudy oil that was filtered to afford the desired material (192.5 g, 95%) as a yellow oil which was used without further purification., 137052-08-5

As the paragraph descriping shows that 137052-08-5 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; PIKE, Kurt, Gordon; BARLAAM, Bernard, Christophe; (85 pag.)WO2017/162605; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

137052-08-5, 1-(Tetrahydro-2H-pyran-4-yl)ethanone is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: The requisite methyl ketone (1equiv), (R)-2-methylpropane-2-sulfinamide (1.5equiv), and Ti(OEt)4 (technical grade, 20% Ti, ?2equiv) in THF (1M), were stirred at reflux for 24-48h. The reaction mixture was cooled to RT and then added to an equal volume of ice water. EtOAc was added and the mixture was stirred vigorously for 15 min after which it was filtered through a pad of Celite. The filter cake was washed with EtOAc. The filtrate was then washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography or triturated with ether to provide the (R)-tert-butanesulfinyl ketimine.

137052-08-5, 137052-08-5 1-(Tetrahydro-2H-pyran-4-yl)ethanone 9877365, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Gilbert, Eric J.; Brunskill, Andrew; Cai, Jiaqiang; Cai, Yaxian; Chu, Xin-Jie; Dai, Xing; Hao, Jinsong; Kuethe, Jeffrey T.; Lai, Zhong; Liu, Hong; Mu, Cuizhi; Qi, Yan; Scott, Jack D.; Taoka, Brandon; Truong, Quang; Walsh, Shawn P.; Wu, Wen-Lian; Cumming, Jared N.; Tetrahedron; vol. 72; 40; (2016); p. 6011 – 6020;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics