Category: Tetrahydropyrans

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 tetrahydro-4H-pyran-4-one (1.0 g, 10.0 mmol) in cold (0 C.) THF is added 1.0M lithium aluminum hydride in THF (5 mL, 5.0 mmol). The reaction mixture is stirred at 0 C. for 15 min. followed by the sequential addition of water (0.190 mL), 5M sodium hydroxide (0.190 mL), and water (0.190 mL) and Et2O. The mixture is filtered, and the filtrate is evaporated to give tetrahydro-4H-pyran-4-ol, which is dissolved in dichloromethane (30 mL). To the solution is added rhodium (II) acetate dimer (44 mg) followed by ethyl diazoacetate (1.25 g, 11.0 mmol). The reaction mixture is stirred at RT for 40 min. The reaction mixture is diluted with ethanol, filtered through celite, and the filtrate is evaporated and the residue is vacuum distilled at 150 C. to give 1.67 g of the product 409. 1H NMR (CDCl3) delta 4.21 (q, 2H), 4.11 (s, 2H), 3.95 (dt, 2H), 3.59 (m, 1H), 3.42 (dt, 2H), 1.91 (m, 2H), 1.62 (m, 2H), 1.28 (t, 3H); MS: m/z 189 (M++1).

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

Reference£º
Patent; Aventis Pharmaceuticals Inc.; US2005/26916; (2005); 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.1172623-99-2,tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

1H (11.53 g, 35.03 mmol) was dissolved in dichloromethane (130 ml), and cooled to 0C. Dess-Martin periodinane(29.72 g, 70.06 mmol) was added in batches to the reaction solution, which was allowed to warm spontaneouslyto room temperature and undergo reaction for 4 hours. The temperature was lowered to 0C, and a saturated sodiumbicarbonate solution (60 ml) was added dropwise to the reaction solution, followed by stirring for 20 min and filtration.The filtrate was allowed to settle and be partitioned, and the aqueous phase was extracted with methyl t-butyl ether (60ml33). The organic phases were combined, washed with a saturated sodium bicarbonate solution (30 ml32), dried byaddition of anhydrous sodium sulfate thereto, filtered, concentrated, and separated by column chromatography (petroleumether/ethyl acetate (v/v) = 10:1 to 4:1), to obtain a white crystalline powder 1I (10.85 g, yield 94.7%).MS m/z (ESI):272.0 [M-55];1H NMR (400 MHz, DMSO-d6): delta7.29 – 7.13 (m, 4H), 4.77 – 4.75 (d, 1H), 4.22-4.02(m, 3H), 2.75-2.70 (m, 2H), 1.23 (s, 9H).

The synthetic route of 1172623-99-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Sichuan Haisco Pharmaceutical Co., Ltd.; ZHANG, Chen; WANG, Jianmin; LI, Caihu; WEI, Yonggang; (64 pag.)EP3159344; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

19752-84-2, Tetrahydro-2H-pyran-3-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound 2 (300 g, 2.9 mol) was dissolved in 3000 g of dichloromethane and sodium acetate (287 g, 3.5 mol) was added.TEMPO 6g, add sodium dichloroisocyanurate (374g, 1.7mol) in batch at 25C, maintain the reaction at 25C for 2h, filter,The organic phase was dried with 200g of anhydrous sodium sulfate, filtered and concentrated in a water pump and distilled to collect the oil temperature of 120C and the top temperature of 90C.250 g of a colorless oily liquid having a purity of 99% and a yield of 83%.

The synthetic route of 19752-84-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Haimen Huaxiang Pharmaceutical Technology Co., Ltd.; Yong Dawei; Cao Zhong; Yang Shaoqiang; Lu Yi; Zhou Guang; Xu Benquan; (4 pag.)CN107382928; (2017); A;,
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.1240390-36-6,tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

To a solution of 5,7-dichloro-3H-pyrido[3,4-d]pyridazin-4-one (100 mg) in NMP (1 ml) in a microwave tube DIPEA (0.107 ml) and ((3R,4R)-4-amino-tetrahydro-pyran-3-yl)- carbamic acid ter-butyl ester (133 mg) was added. The tube was capped and heated on a sandbath at 10000 for 3 days. After cooling to room temperature the reaction mixture was diluted with 30 ml of EtOAc and washed with brine (2 x 50 ml). Aqueaous phases were re-extracted with EtOAc (30 ml) and combined organic phases were dried and evaporated to dryness leaving a yellow solid. Purification was effected via flash chromatography.

As the paragraph descriping shows that 1240390-36-6 is playing an increasingly important role.

Reference£º
Patent; NOVARTIS AG; THOMA, Gebhard; BUEHLMAYER, Peter; VAN EIS, Maurice; SMITH, Alexander Baxter; WO2014/27300; (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.134419-59-3,Tetrahydro-2H-pyran-4-yl methanesulfonate,as a common compound, the synthetic route is as follows.

In a glass flask having inner volume of 20 ml provided with stirrer, the thermometer, and the reflux condenser, 1.85 g (10.2mmol) of tetrahydropyranyl 4-methanesulfonate, potassium cyanide 1.0g (15.4mmol), and 10 ml of dimethyl sulfoxide were added and the mixture was reacted at 80 degrees C for 7 hours. After completion of the reaction, the reaction mixture was analyszed by gas chromatography (internal standard method), 0.50 g of 4-cyanotetrahydropyran was obtained (reaction yield: 44%).

The synthetic route of 134419-59-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UBE INDUSTRIES LIMITED; NISHINO, SHIGEYOSHI; HIROTSU, KENJI; SHIMA, HIDEYOSHI; IWAMOTO, KEIJI; HARADA, TAKASHI; (13 pag.)JP5673729; (2015); B2;,
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.14774-36-8,(Tetrahydropyran-3-yl)methanol,as a common compound, the synthetic route is as follows.

Step 1 : To a solution of (tetrahydro-2H-pyran-3-yl)methanol (300 mg, 2.58 mmol) and TEA (522 mg, 5.17mmol) in dichloromethane (10 ml_) was added methanesulfonyl chloride (355 mg, 3.10 mmol) at 0 C and the reaction was allowed to warm to 20 C and stirred for 1 hour. The solution was washed with sat. aq. NaHCO3 (2 ml_), H2O (3×2 ml_), brine (1 ml_), dried and concentrated to give (tetrahydro-2H-pyran-3-yl)methyl methanesulfonate (500 mg), which was used in the next step directly

As the paragraph descriping shows that 14774-36-8 is playing an increasingly important role.

Reference£º
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; JESSING, Mikkel; (126 pag.)WO2016/55618; (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.1768-64-5,4-Chlorotetrahydropyran,as a common compound, the synthetic route is as follows.

A solution of 4-chlorotetrahydro-2H-pyran (1.2 g, 10 mmol) in THF (5 mL) was added dropwise to a mixture of Mg (486 mg, 20 mmol) and I2 (1 mg) at 70oC. The mixture was stirred at 50oC for 0.5 h, diluted with THF (5 mL) and used directly. To a solution of (tetrahydro-2H- pyran-4-yl)magnesium chloride (4.14 mL, 1 M in THF) was added N-8-7_1 (500 mg, 1.38 mmol) in THF (5 mL) at 0C under N2. Then the mixture was stirred at 15oC for another 18 hrs. The reaction mixture was quenched with sat. NH4Cl (5 mL), and the resulting mixture was extracted with EtOAc (2 x 10 mL). The combined organic layer was washed with brine (5 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash column (0-15% EtOAc in PE) to give N-8-17_1 (350 mg, 57%) as a solid. 1H NMR (400 MHz, CDCl3) delta 4.08-3.91 (m, 2H), 3.43-3.31 (m, 2H), 3.31-3.25 (m, 1H), 1.98- 1.91 (m, 2H), 1.91-1.80 (m, 1H),1.70-1.50 (m, 10H), 1.50-1.41 (m, 2H), 1.41-1.32 (m, 5H), 1.32-1.15 (m, 9H), 1.15-0.92 (m, 6H), 0.92-0.83 (m, 7H), 0.65 (s, 3H) .

The synthetic route of 1768-64-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SAGE THERAPEUTICS, INC.; SALITURO, Francesco, G.; ROBICHAUD, Albert, J.; MARTINEZ BOTELLA, Gabriel; HARRISON, Boyd, L.; GRIFFIN, Andrew; LA, Daniel; (299 pag.)WO2018/75698; (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.14774-37-9,Tetrahydropyran-4-methanol,as a common compound, the synthetic route is as follows.

Step 2: Synthesis of compound B3Prepared as described by adaptation of the following literature reference: Radziszewski, J.G. et al. J. Am. Chem. Soc. 1993, 115, 8401.To a solution of 97 g (810 mmol) of compound B2 in 2-methyltetrahydrofuran (190 mL) are added 165 mL of 50% aqueous NaOH solution. To this stirred suspension is added dropwise with cooling a solution of p-toluene-sulfonylchloride (283 g, 1.46 mol) in 2-methyltetrahydrofuran (280 mL). The reaction is stirred at 30-35 C for 18 h. The suspension is poured into a mixture of ice- water (280 mL) and aqueous HC1 solution (37%, 203 mL). After addition of methylcyclohexane (1.4 L) and further ice-water (0.2 L), the reaction mixture is stirred for 2 h in an ice-bath. The resulting crystalline precipitate is isolated by filtration and washed with methylcyclohexane (0.5 L) and water (0.5 L). Drying under reduced pressure at 40 C gave 216 g of compound B3 as white crystalline solid. Yield: 99%, ES-MS: m/z 271 [M+H]; ]H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.19 – 1.35 (2 H, m), 1.54 – 1.63 (2 H, m), 1.85 – 2.02 (1 H, m), 2.45 (3 H, s), 3.28 – 3.39 (2 H, m), 3.86 (2H, d, J=6.60 Hz), 3.93 (2 H, dd, J=11.37, 4.52 Hz), 7.35 (2 H, d, J=9.29 Hz), 7.78 (2 H, d, J=8.31 Hz)

As the paragraph descriping shows that 14774-37-9 is playing an increasingly important role.

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

388109-26-0, Ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 To a solution of ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate (1.0 g, 5.81 mmol) in DCM (30 mL) was added DIPEA (1.22 mL, 6.97 mmol) and Tf2O (1.08 mL, 6.39 mmol) at -78 C., then it was warmed up to room temperature and stirred at room temperature for 2 h, the solution was diluted with DCM, washed with Sat. NaHCO3, brine, dried and concentrated to give ethyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydro-2H-pyran-4-carboxylate as crude product (2 g).

As the paragraph descriping shows that 388109-26-0 is playing an increasingly important role.

Reference£º
Patent; Global Blood Therapeutics, Inc.; Metcalf, Brian W.; US2015/209443; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

25637-16-5, 4-Bromotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a 20 mL pressure-resistant reaction tube, 40 mg (0.2 mmol) of 2- (4-methoxyphenoxy) pyridine was added,(0.6 mmol) of 4-bromotetrahydropyran, 6 mg (0.01 mmol) of dichlorobis (4-methylisopropylphenyl) ruthenium, 55 mg (0.4 mmol) of potassium carbonate,11 mg (0.06 mmol) 1-adamantane acid, 1.5 mL benzene,Sealed under nitrogen, heated to 120 C reaction, stirred for 24 hours, after the reaction, the column chromatography,The desired product 2- (4-tetrahydropyranylphenoxy) pyridine 33mg, 58% yield.

25637-16-5 4-Bromotetrahydropyran 13349654, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Anyang Normal University; Li Gang; Yang Suling; Sun Kai; Liu Leilei; Li Zhimin; Lv Xulu; (6 pag.)CN107089940; (2017); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics