Category: 29943-42-8

29943-42-8, Dihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Tetrahydro-2H-pyran-4-carbonitrile. A solution of tetrahydro-4H-pyran-4-one (25 g, 250 mmol) and toluenesulfonylmethyl cyanide (53.7 g, 275 mmol) dissolved in ethylene glycol dimethylether (1 L) was cooled to 0 C. Added dropwise over 30 min was a solution of potassium t-butoxide (56 g, 500 mmol) dissolved in t-butanol (350 mL) and ethylene glycol dimethylether (150 mL). After stirring the resulting mixture for 3 h at room temp, diethyl ether (1 L) was added and the organic phase was washed with saturated aqueous NaHCO3. The organic phase was dried (Na2SO4) and concentrated. The residue was distilled at 39 C. 1.7 mm Hg to give the title compound as a colorless oil (10.87 g, 39% yield). 1H NMR (300 MHz, CDCl3) delta: 3.91-3.83 (2H, m), 3.61-3.54 (2H, m), 2.89-2.80 (1H, m), 1.97-1.78 (4H, m)., 29943-42-8

The synthetic route of 29943-42-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Bristol-Myers Squibb Company; US2008/4265; (2008); 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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

A) tert-butyl 2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate [0431] A solution of tetrahydro-4H-pyran-4-one (2.50 g) and tert-butyl hydrazinecarboxylate (3.47 g) in methanol (10 mL) was stirred at room temperature for 1 hr, and concentrated under reduced pressure. The residue was dissolved in THF (25 mL), acetic acid (4.3 mL) and sodium borohydride (0.525 g) were added thereto, and the mixture was stirred at 0C for 1 hr. To the reaction mixture was added 8N aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.34 g). 1H NMR (300 MHz, CDCl3) delta 1.35-1.54 (11H, m), 1.77 (2H, dd, J = 12.1 Hz, 2.3 Hz), 2.98-3.15 (1H, m), 3.40 (2H, td, J = 11.3 Hz, 2.3 Hz), 3.96 (3H, dt, J = 11.5 Hz, 3.7 Hz), 6.03 (1H, brs).

29943-42-8, 29943-42-8 Dihydro-2H-pyran-4(3H)-one 121599, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; NARA, Hiroshi; DAINI, Masaki; KAIEDA, Akira; KAMEI, Taku; IMAEDA, Toshihiro; KIKUCHI, Fumiaki; EP2857400; (2015); 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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

To a stirred suspension of 4 A powdered molecular sieves and dihydro-2H-pyran-4(3H)-one (27.8 mL, 300 mmol) in ethanol (300 mL), tetrahydrofuran (150 mL) was added methanamine (180 mL, 360 mmol) dropwise and stirred overnight at room temperature. Reaction mixture was cooled to 0-5 C., then was added sodium borohydride (22.67 g, 599 mmol) lot wise for 20 min and stirred for 6 h at room temperature. Reaction mixture was quenched with 10% solution of NaHCO3 (300 mL) and concentrated under reduced pressure to remove the volatiles. The above reaction mixture was diluted with ethyl acetate (300 mL) and filtered through CELITE bed filter. The CELITE bed was washed with ethyl acetate (100 mL). The aqueous layer was separated and extracted with ethyl acetate (2*100 mL). The combined organic layer was dried over sodium sulfate and concentrated under reduced pressure to get crude 866A (25 g, 211 mmol, 70.3% yield) as yellow liquid and taken for next step without further purification. LC-MS Anal. Calc’d. for C6H13NO, 115.10. found (M+H) 116.10 Tr=0.36 min (Method U)., 29943-42-8

29943-42-8 Dihydro-2H-pyran-4(3H)-one 121599, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; Balog, James Aaron; Cherney, Emily Charlotte; Guo, Weiwei; Huang, Audris; Markwalder, Jay A.; Seitz, Steven P.; Shan, Weifang; Williams, David K.; Murugesan, Natesan; Nara, Susheel Jethanand; Roy, Saumya; Thangavel, Soodamani; Sistla, Ramesh Kumar; Cheruku, Srinivas; Thangathirupathy, Srinivasan; Kanyaboina, Yadagiri; Pulicharla, Nagalakshmi; (495 pag.)US2016/289171; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

29943-42-8, Dihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1: Synthesis of Compound A2To a solution of 75 g (0.75 mol) of compound Al in THF (150 mL) is added a suspension of 28.4 g (0.75 mol) L1AIH4 in THF (600 mL) under nitrogen atmosphere maintaining the temperature below 30 C with the aid of an ice-bath. Then the reaction is allowed to warm to room temperature and stirred for 5 h. The reaction is quenched by addition of saturated aqueous NH4C1 solution until effervescence ceased. The resulting precipitate is removed by filtration through Celite and washed with THF (150 mL). The filtrate is concentrated under reduced pressure to afford 71.1 g of compound A2 as a pale yellow oil. Yield: 92%, ]H NMR (500 MHz, CHLOROFORM-d) delta ppm 1.54 (2 H, m, 7=13.37, 9.55, 9.55, 4.22 Hz), 1.81 – 1.92 (2 H, m), 2.11 (1 H, br. s.), 3.38 – 3.47 (2 H, m), 3.83 (1 H, tt, 7=9.10, 4.38 Hz), 3.94 (2 H, dt, 7=11.88, 4.15 Hz), 29943-42-8

29943-42-8 Dihydro-2H-pyran-4(3H)-one 121599, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; ZINDELL, Renee, M.; ERMANN, Monika; WO2011/109324; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

29943-42-8, Dihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 12: tetrahydro-2H-pyran-4-ylhydrazine, trifluoroacetate; Tetrahydro-4H-pyran-4-one (Apollo; 924 muL; 10.0 mmol) and te/f-butyl carbazate (1 .39 g; 10.50 mmol) were dissolved in ethanol (10 mL) and stirred at room temperature overnight. The solvent was removed in vacuo and the residue was redissolved in 1 :1 wate?acetic acid (10 mL) and sodium cyanoborohydride (660 mg; 10.50 mmol) added. The mixture was stirred at room temperature for 3 hours and then 2:1 ethyl acetate: 10% aqueous potassium carbonate (50 mL) added. The organic layer was separated, washed with brine, passed through a hydrophobic frit and the solvent removed in vacuo. The residue was redissolved in DCM (10 mL) and trifluoroacetic acid (1 mL) added and the mixture stirred overnight. The solvent was removed in vacuo to yield Intermediate 12 as a semi-solid slurry which was used directly without any purification. 1H NMR: (DMSOd6, 400MHz) delta 4.08-3.76 (2 H, m), 3.41 -3.27 (2 H, m), 3.23-3.14 (1 H, m), 1 .99-1.83 (2 H, m), 1 .59-1.43 (2 H, m). LC/MS: 1 17 (M+H)+.

29943-42-8, The synthetic route of 29943-42-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK SERONO S.A.; QUATTROPANI, Anna; BAKER-GLENN, Charles; BLACKABY, Wesley; KNIGHT, Chris; WO2010/142628; (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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

To a solution of tetrahydropyran-4-one (71.6 g, 715 mmol) in methanol (2 L) was added tert-butylcarbazate (100 g, 758 mmol) at ambient temp. The mixture was stirred at ambient temp for 20 h. The reaction mixture was concentrated under reduced pressure to dryness to afford a white solid (154 g). To a suspension of the white solid (154 g, 715 mmol) in water (1 L) was added acetic acid (500 mL, 8.73 mol) and the mixture was stirred for 30 min to get a clear solution. To this solution, solid NaCNBH3 (44.5 g, 708 mmol) was added portion-wise. The mixture was stirred at ambient temp for 2 h. The mixture was then transferred to a 12 L flask, cooled to 0 C., and quenched with 1N NaOH (8.73 L, 8.73 mol). The mixture was extracted with CH2Cl2 (3*3 L) and dried over Na2SO4. The organic layer was filtered and concentrated to afford a white solid (164 g, contains ~15% of N-acetyl-N’-Boc-hydrazine derivative). Chromatography [silica, ethyl acetate/MeOH (95:5] gave 94 g of 90% pure boc-hydrazine. A solution of boc-hydrazine (50 g, 231 mmol) in methanol (500 mL) was added a solution of HCl in dioxane (462 mL, 1.85 mol, 4.0 M). The mixture was stirred at ambient temp overnight. Concentration of the reaction mixture under reduced pressure afforded the title compound as a white solid (43 g, 98%). 400 MHz 1H NMR (DMSO) delta 3.85-3.82 (m, 2H), 3.27-3.21 (m, 2H), 3.13-3.05 (m, 1H), 1.88-1.84 (m, 2H), 1.48-1.38 (m, 2H). MS: (M+H m/z=117.2).

29943-42-8, As the paragraph descriping shows that 29943-42-8 is playing an increasingly important role.

Reference£º
Patent; Pfizer Inc; US2009/30003; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

29943-42-8, Dihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

29943-42-8, A mixture of tetrahydro-4H-pyran-4-one (31.7mL, 0.34mol) and tert-butylcarbazate (47.7g, 0.36mol) in EtOH (50OmL) was stirred at ambient temperature overnight. The reaction mixture was evapotrated and the reisdue suspended in HOAc-H2O (1:1 / 50OmL). NaCNBH3 (22.64g,0.36mol) was added and the mixture was stirred at ambient temperature for 2.5hr. The reaction mixture was suspended in EtOAc-10% K2CO3 (2:1 / 75OmL). The organic layer was separated, washed with brine (2 x 40OmL) and dried (MgSO4). Filtration and evaporation of the solvent and trituration of the residue with hexane afforded the product as a white amorphous solid(47.5g, 64%). 1H NMR (CDCl3) 6.10 (IH, br s), 3.99-3.35 (5H, m), 3.06 (IH, m), 1.79-1.35(4H, m), 1.46 (9H, s)

29943-42-8 Dihydro-2H-pyran-4(3H)-one 121599, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; JAMES BLACK FOUNDATION; WO2007/135350; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

29943-42-8, Dihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,29943-42-8

Step 1 Methylmagnesium bromide (3.66 mL, 10.99 mmol) was added dropwise via syringe to a solution of dihydro-2H-pyran-4(3H)-one (1 g, 9.99 mmol) in Diethyl ether (50 mL) at 0 C. and stirred at this temp for 1 hr before warming up to RT. The reaction was quenched with sat. ammonium chloride and extracted with ether. The organic layer was washed with brine, collected, dried over MgSO4, filtered and evaporated to give the crude product 4-methyltetrahydro-2H-pyran-4-ol (1 g, 86% yield) as an oil. 1H NMR (400 MHz, CHLOROFORM-d) delta 3.82-3.73 (m, 2H), 3.73-3.66 (m, 2H), 1.74-1.64 (m, 3H), 1.54 (ddt, J=13.7, 4.6, 2.1 Hz, 2H), 1.41 (br. s, 1H), 1.28 (s, 3H).

29943-42-8 Dihydro-2H-pyran-4(3H)-one 121599, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P. V. K. Suresh; Scola, Paul Michael; US2013/115190; (2013); 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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

[0521] To the mixture of tetrahydro-4H-pyran-4-one (15.00 g, 149.82 mmol), dimethyl carbonate (33.74 g, 374.55 mmol) in THF (300.00 mL) was added NaH (14.98 g, 374.55 mmol, 60% purity) by protions at 0 C. The mixture was stirred under N2 at 0 C for 30 min, then at 15 C for 30 min. Then the mixture was warmed to 45 C and stirred for 15 h. TLC (petroleum ether/EtOAc=3: 1, Rf=0.6) showed one new main spot. The reaction mixture was poured into the mixture of icy 1 N HCl (600 mL) and extracted with EtOAc (600 mLx3). The combined organic layers were washed with brine (800 mLx2), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (Si02, petroleum ether/EtOAc=l :0 to 10: 1) to afford the title compound (7.75 g 33%) as colorless oil. 1H NMR (400 MHz, DMSO-i/6) delta 11.78 (s, 1H), 4.14-4.10 (m, 1H), 4.07-3.95 (m, 1H), 3.86 (t, J = 5.6 Hz, 2H), 3.78-3.77 (m, 3H), 2.40 (t, J= 5.6 Hz, 2H)., 29943-42-8

The synthetic route of 29943-42-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; KADMON CORPORATION, LLC; OLSZEWSKI, Kellen; KIM, Ji-In; POYUROVSKY, Masha; LIU, Kevin; BARSOTTI, Anthony; MORRIS, Koi; (344 pag.)WO2016/210330; (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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

To a solution of dimethyl carbonate (22.50 g, 249.78 mmol, 5.00 equiv) in tetrahydrofuran (70 ml_) at 0 C was added sodium hydride (6.00 g, 150.00 mmol, 3.00 equiv, 60%). The mixture was stirred at 15 C for 1 h and then the mixture was cooled to 0 C and oxan-4-one (5.00 g, 49.940 mmol, 1.00 equiv) was added dropwise. The resulting solution was stirred for 2 h at 60 C in an oil bath. The reaction was then quenched by the addition of water and the pH adjusted to 6 with hydrogen chloride (2N). The resulting solution was extracted with ethyl acetate (3×20 ml_) and the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (10/90). The collected fractions were combined and concentrated under vacuum to yield methyl 4-oxooxane-3- carboxylate as yellow oil.

29943-42-8, 29943-42-8 Dihydro-2H-pyran-4(3H)-one 121599, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; LANTER, James C.; WALL, Mark; SUI, Zhihua; (0 pag.)WO2019/171278; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics