Category: 1194-16-7

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

To a solution of benzyloxycarbonyl-a-phosphonoglycine trimethyl ester (1.163 g, 3.52 mmol) in dry DCM (20 mL) was added DBU (0.534 g, 3.52 mmol) dropwise at 0C. Then a solution of compound cap 3a (1.8 g, 14.08 mmol) in dry DCM (20 mL) was added dropwise at 0C. The reaction mixture was stirred at 25C for 3 days. After removal of the solvent, the residue was purified using Si02 chromatography (e luting with petroleum ether/ ethyl acetate = 5: 1 to 3: 1) to providecompound cap 3b as white solid (0.15 g, 13% yield). 1H NMR (CDC13): delta 7.30-7.35 (m, 5 H), 5.11 (s, 2 H), 3.82-3.88 (m, 3 H), 3.09-3.16 (m, 2 H), 1.84 (s, 2 H), 1.48 (s, 2 H), 1194-16-7

As the paragraph descriping shows that 1194-16-7 is playing an increasingly important role.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; YU, Wensheng; TONG, Ling; KOZLOWSKI, Joseph A.; SELYUTIN, Oleg; CHEN, Lei; KIM, Jae-Hun; SHA, Deyou; RIZVI, Razia; SHANKAR, Bandarpalle; HU, Bin; ZHONG, Bin; WAI, Dahai; HAO, Jinglai; WEI, Wei; JI, Tao; ZAN, Shuai; WO2014/110705; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1194-16-7, 2,2-Dimethyltetrahydropyran-4-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 2,2-dimethyloxan-4-one (2.00 g, 15.6 mmol), sulfur (500 mg, 15.6 mmol), cyanamide (656 mg, 15.6 mmol and pyrrolidine (13 muL¡¤, 0.156 mmol) was stirred in isopropanol (3 mL) at room temperature for 3h. The reaction mixture was filtered to remove excess sulfur and chromatographed on silica, eluting with 5% MeOH in DCM to afford the title compound as a yellow solid (2.87 g, 47 ). 1H NMR (500 MHz, CDC13) delta 4.94 (br. s., 2H), 4.64 (t, J=1.8 Hz, 2H), 2.56 (s, 2H), 1.34 – 1.30 (s, 6H)., 1194-16-7

The synthetic route of 1194-16-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BROMIDGE, Steven; BURCH, Jason; HEIFETZ, Alexander; KRULLE, Thomas; MONTALBETTI, Christian A.G.N.; PEI, Zhonghua; PEREZ-FUERTES, Yolanda; TRANI, Giancarlo; (223 pag.)WO2016/1341; (2016); 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.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

-BuLi (26.3 ml, 1.6 M in hexane, 42 mmol) was added dropwise to a solution of 4- bromo-toluene (7.70 g, 45 mmol) in THF (100 ml) at -78 C under N2. The resulting mixture was stirred at -78 C for 30 min and a solution of tetrahydro-2,2-dimethyl-4H- pyran-4

1194-16-7, The synthetic route of 1194-16-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; TREVENA, INC.; VIOLIN, Jonathan D.; SOERGEL, David G.; (177 pag.)WO2017/106547; (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.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

To a solution of 7,7-dimethyloxepan-4-one and 2,2-dimethyloxepan-4-one (2.6 g, 18.3 mmol) and pyrrolidine (85 mg, 1.2 mmol) in dimethyl sulfoxide (20 mL) was slowly added ethyl diazoacetate (1.39 g, 12.2 mmol). After addition, the reaction was stirred at 22 C for 16 h and poured into water (30 mL). The mixture was then extracted with ethyl acetate (3 x 30 mL).The combined organic layers were washed with water (2 x 30 mL) and brine (30 mL), dried over sodium sulfate and concentrated to dryness in vacuo. The residue was purified by column chromatography (silica gel, 100-200 mesh, 0 to 18% ethyl acetate in petroleum ether) to afford a mixture of three regio-isomers (900 mg, 20.6% yield) as yellow oil. The regio-isomers were separated by SFC to afford: Peak 1 (Rention time 3.31 min), ethyl 5,5-dimethyl-4,5,7,8-tetrahydro-1H-oxepino[4,5-c]pyrazole-3-carboxylate (200 mg): 1H MR (400 MHz, CDC13) delta 4.38 – 4.33 (m, 2H), 3.88 (t, J = 6.0 Hz, 2H), 3.11 (s, 2H), 2.97 (t, J= 6.00 Hz, 2H), 1.37 (t, J= 6.00 Hz, 2H), 1.21 (s, 6H) Peak 2 (Rention time 3.37 min), ethyl 7,7-dimethyl-4,5,7,8-tetrahydro-1H-oxepino[4,5-c]pyrazole-3-carboxylate (150 mg) as a yellow oil: NMR (400 MHz, CDC13) delta 4.39 – 4.34 (m, 2H), 3.92 – 3.87 (m, 2H), 3.08 – 3.03 (m, 2H), 2.98 (s, 2H), 1.38 (t, J= 6.0 Hz, 3H), 1.23 (s, 6H) Peak 3 (Rention time 6.30 min), ethyl 6,6-dimethyl-4,5,6,8-tetrahydro-1H-oxepino[3,4-c]pyrazole-3-carboxylate (150 mg) as a yellow oil: 1H MR (400 MHz, CDC13) delta 4.68 (s, 2H), 4.40 – 4.35 (m, 2H), 3.00 – 2.92 (m, 2H), 1.95 – 1.88 (m, 2H), 1.39 (t, J = 6.0 Hz, 3H), 1.33 (s, 6H). SFC conditions: Column: Chiralpak AD-3 150×4.6mm I D., 3um Mobile phase: A: C02 B: ethanol (0.05% DEA) Gradient: from 5% to 40% of B in 5 min and hold 40% for 2.5 min, then 5% of B for 2.5 min Flow rate: 2.5mL/min Column temp.: 35C Column: Chiralpak AY 150×4.6mm ID., 3um Mobile phase: A: C02 B: iso-propanol (0.05% DEA) Gradient: from 5% to 40% of B in 5 min and hold 40% for 2.5 min, then 5 for 2.5 min Flow rate: 2.5mL/min Column temp.: 35C, 1194-16-7

The synthetic route of 1194-16-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; PATEL, Snahel; HAMILTON, Gregory; STIVALA, Craig; CHEN, Huifen; ZHAO, Guiling; (1236 pag.)WO2017/4500; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1194-16-7, 2,2-Dimethyltetrahydropyran-4-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a 2 L round bottomed flask, 2,2-dimethyldihydro-2H-pyran-4(3H)-one (10.4 g, 0.08 mol) was dissolved in water (500 mL) along with sodium metabisulfite (7.7 g, 0.04mol). The mixture was allowed to stir at rt for 1.5 h, then benzylpiperazine (14.2 g,0.08 mol) was added. The mixture was stirred for 2 h and potassium cyanide (8.42 g,0.13 mol) was added to the reaction mixture. After stirring at rt for 2 days the solidformed was filtered and dried, to give the title compound as a white solid (15.4 g, yield61%). HPLC-MS (Method A): Ret, 1.98 mm; ESl-MS m/z, 314.1 (M+1)., 1194-16-7

1194-16-7 2,2-Dimethyltetrahydropyran-4-one 1738159, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; GARCIA-LOPEZ, Monica; ALMANSA-ROSALES, Carmen; LLORENTE-FERNANDEZ, Ana Virginia; CHRISTMANN, Ute; RODRIGUEZ ESCRICH, Sergio; (355 pag.)WO2017/198339; (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.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

A solution of 2,2-dimethyltetrahydropyran-4-one (133) (115 g, 0.9 mol, 1.0 eq.) in anhydrous THF (600 mL) was cooled to -78 C and to it was added LDA (2.0 M, 538 mL, 1.08 mol, 1.2 eq.) drop wise under N2 keeping the internal temperature below -65 C. The resulting solution was stirred at -78 C for 20 min. A solution of N-phenyl- bis(trifluoromethanesulfonimide) (353 g, 0.99 mol, 1.1 eq.) in anhydrous THF (1900 mL) was added to the above solution slowly keeping the internal temperature below -65 C. The reaction mixture was warmed to room temperature slowly and stirred overnight. The reaction was quenched with saturated aqueous sodium bicarbonate solution, and extracted with MTBE (2 L X 2). The combined organic layers was washed with 10% aqueous NaOH solution (1 L X 2), brine (500 mL X 2), dried over Na2S04, filtered and concentrated to give crude title triflate product mixture as dark brown oil. The crude product was extracted with hexanes (2 L X 5) and the combined hexanes extracts was purified by column chromatography (directly loaded onto silica gel, Hexanes? 15% ethyl acetate in hexanes, R/= 0.6, visualized with KMn04 stain) to give 200 g of the triflate product mixture (134) (a mixture of 2,2-dimethyl-3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate and 6,6-dimethyl-3 ,6-dihydro-2H-pyran-4-yltrifluoromethanesulfonate ratio = 80.6: 19.4 by GCMS) as a light yellow liquid (~ 90% purity by GC-MS and 1H NMR). This was taken to the next step without further purification.

1194-16-7, 1194-16-7 2,2-Dimethyltetrahydropyran-4-one 1738159, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; AMGEN INC.; ALLEN, Jennifer R.; CHEN, Jian J.; FROHN, Michael J.; HU, Essa; LIU, Qingyian; PICKRELL, Alexander J.; RUMFELT, Shannon; RZASA, Robert M.; ZHONG, Wenge; WO2011/143365; (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.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

General procedure: A solution of trimethyl phosphonoacetate (9.36 mmol) in THF (7 mL, 1.34 M) was added dropwise to sodium hydride (60% in mineral oil, 9.75 mmol) suspended in THF (35 mL) at 0 C. After 40 min, the pyranone (7.80 mmol), in THF (7 mL, 1.11 M), was added dropwise and the flask was heated to 25 C. After 19 h, the mixture was cooled to room temperature and quenched with saturated aqueous NH4Cl (10 mL). The precipitate was removed by filtration and the layers were separated. The aqueous layer was extracted with ether (2*20mL) and the organic fractions were combined, dried (MgSO4), filtered, and concentrated under vacuum. The crude material was purified as indicated., 1194-16-7

As the paragraph descriping shows that 1194-16-7 is playing an increasingly important role.

Reference£º
Article; Shouksmith, Andrew E.; Evans, Laura E.; Tweddle, Deborah A.; Miller, Duncan C.; Willmore, Elaine; Newell, David R.; Golding, Bernard T.; Griffin, Roger J.; Australian Journal of Chemistry; vol. 68; 4; (2015); p. 660 – 679;,
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.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

Cap- 188, step aTo a solution of 2,2-dimethyldihydro-2H-pyran-4(3H)-one (2 g, 15.60 mmol) in 50 niL of MeOH was slowly added sodium borohydride (0.649 g, 17.16 mmol). The resulting mixture was stirred at room temperature for 3 hours. To the mixture was then added 1 N HCl aqueous solution until it crosses into acidic pH range and then extracted with EtOAc (3X). The combined organic layers were dried withMgS04 and concentrated to afford Cap-188, step a (1.9 g) as clear oil. The product was used in the next step without purification. XH NMR (400 MHz, CDCI3) delta ppm 3.91 – 4.02 (1 H, m), 3.79 – 3.86 (1 H, m), 3.63 (1 H, td, J=12.05, 2.51 Hz), 1.82 – 1.93 (2 H, m), 1.40 – 1.53 (1 H, m), 1.29 – 1.38 (1 H, m), 1.27 (3 H, s), 1.20 (3 H, s), 1194-16-7

The synthetic route of 1194-16-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; BELEMA, Makonen; SRINIVASU, Pothukanuri; BENDER, John A.; LOPEZ, Omar D.; CHEN, Qi; RAMPULLA, Richard A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; MEANWELL, Nicholas A.; WO2012/21591; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1194-16-7, 2,2-Dimethyltetrahydropyran-4-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example B15a and B15b: 7,7-dimethyloxepan-4-one and 2,2-dimethyloxepan-4-one Into a 100-mL 3 -necked round-bottom flask purged and maintained with nitrogen atmosphere was placed a solution of 2,2-dimethyloxan-4-one (1.3 g, 10.14 mmol, 1.00 equiv) in dichloromethane (40 mL) and boron fluoride ethyl ether (1.4 mL, 1.10 equiv). TMSCHN2 (6 mL, 1.10 equiv, 2mol/L in hexane) was added dropwise at -30C. The resulting solution was stirred for 1 h at -30 C and TLC (PE:EA=5:l)showed conversion was almost complete. The reaction was quenched with saturated sodium bicarbonate, extracted with 3×100 mL of dichloromethane. The organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 1.5g of crude yellow oil as a mixture of 2,2-dimethyloxepan-4-one and 7,7- dimethyloxepan-4-one ., 1194-16-7

The synthetic route of 1194-16-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F.HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BROOKFIELD, Frederick; BURCH, Jason; GOLDSMITH, Richard A.; HU, Baihua; LAU, Kevin Hon Luen; MACKINNON, Colin H.; ORTWINE, Daniel Fred; PEI, Zhonghua; WU, Guosheng; YUEN, Po-wai; ZHANG, Yamin; WO2014/23258; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1194-16-7, 2,2-Dimethyltetrahydropyran-4-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To sodium hydride (23.8 mmol) in THF (80 ml) at [0C] was added trimethyl phosphonoacetate (22.86 mmol). The reaction mixture was stirred for 15 minutes and a solution [OF EXAMPLEL] (A) (20.6 mmol) in THF (20 ml) was added. After 20 hours at ambient temperature the reaction was quenched by addition of an aqueous ammonium chloride solution. Extraction with ethyl acetate, drying (sodium sulfate) and evaporation yielded the crude product. Purification by flash column chromatography (silica gel) eluting with ethyl acetate-hexane (1: 5) gave the desired product., 1194-16-7

1194-16-7 2,2-Dimethyltetrahydropyran-4-one 1738159, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Signal Pharmaceuticals, Inc.; WO2003/105774; (2003); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics