Category: Tetrahydropyrans

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.25637-16-5,4-Bromotetrahydropyran,as a common compound, the synthetic route is as follows.

General procedure: To a flame-dried Schlenk tube was charged with vinyl bromide (0.30 mmol, 2 equiv, if solid), unactivated alkyl halide (0.15 mmol, if solid), zinc powder (16.5 mg, 0.30 mmol, 2 equiv), and MgCl2 (14.2 mg, 0.15mmol, 1 equiv). The tube was moved into a dry glovebox, at which point Ni(cod)2 (2.1 mg, 0.008 mmol, 5 mol%) was added. The tube was capped with a rubber septum, and it was moved out of the glovebox. At this point, the vinyl bromide (0.30 mmol, 2 equiv, if liquid) and alkylhalide (0.15 mmol, 1 equiv, if liquid) were added together with solvent (1 mL) and pyridine (11.8 mg, 0.15 mmol, 1 equiv) via a syringe.The mixture was stirred for 16 h under N2 atmosphere at 25 C, and then it was directly loaded onto a column (silica gel) without work-up. The residue in the reaction vessel was rinsed with small amount of CH2Cl2. Flash column chromatography provided the product as a solid or oil. The E/Z ratio of the product was determined by GC-MS. (E)-4-Styryl-1-tosylpiperidine (3): according to the general procedure, column chromatography (silica gel, 7% EtOAc/PE) gave the product (42.5 mg, 0.125 mmol, 83%) as a white solid; mp 140-141 C. 1H NMR (500 MHz, CDCl3): delta = 7.66 (d, J = 8.0 Hz, 2 H), 7.34-7.28 (m, 6 H), 7.20 (t, J = 7.0 Hz, 1 H), 6.31 (d, J = 16.0 Hz, 1 H), 5.97 (dd, J = 7.0,16.0 Hz, 1 H), 3.82-3.80 (m, 2 H), 2.44 (s, 3 H), 2.34-2.29 (m, 2 H), 2.08-2.02 (m, 1 H), 1.83-1.81 (m, 2 H), 1.73-1.70 (m, 1 H), 1.46-1.39 (m, 1 H). 13C NMR (125 MHz, CDCl3): delta = 143.4, 137.1, 133.4, 133.1, 129.5, 128.9, 128.5, 128.2, 127.7, 127.2, 126.0, 46.1, 38.5, 31.2, 21.5. HRMS (ESI): m/z [M + H]+ calcd for C20H24NO2S: 342.1522; found: 342.1525.

25637-16-5, The synthetic route of 25637-16-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Gu, Jun; Qiu, Canbin; Lu, Wenbin; Qian, Qun; Lin, Kunhua; Gong, Hegui; Synthesis; vol. 49; 8; (2017); p. 1867 – 1873;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

693287-79-5, tert-Butyl 2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,693287-79-5

A mixture of tert-butyl 2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate (3.8 g,0.018 mol) and trifluoroacetic acid (20 mL, 0.3 mol) were stirred in dichloromethane (20 mL) for 90 minutes. The mixture was concentrated, and the residue was taken up in acetonitrile (30 mL). l-(2,6-difluoropyridin-3-yl)propan-l-one (2.34 g, 0.0137 mol) was then added, and the resulting mixture was stirred at 75 0C for 72 hours. After cooling to room temperature, the mixture was concentrated, and the residue was purified by flash chromatography on silica gel using a 10-50% hexane:ethyl acetate gradient (flow rate 20 mL/min). The organics were combined and the crude product was then extracted with ethyl acetate. The combined extracts were washed with saturated sodium bicarbonate and then concentrated to afford 2.86 g (83.9 %) of 3-ethyl-6-fIuoro-l-(tetrahydro-2H-pyran- 4-yl)-lH-pyrazolo[3,4-b]pyridine as a white solid. LC/MS (EI) tR 3.5 (Method E), m/z 250 (M++1).

As the paragraph descriping shows that 693287-79-5 is playing an increasingly important role.

Reference£º
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2006/44528; (2006); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

951127-25-6, tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

951127-25-6, tert-Butyl N-[(2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydropyran-3-yl]carboxylate(0.22 g, 0.67 mmol) was dissolved in N,N-dimethylacetamide (3.3 mL).Add 2-(2-thienylsulfonyl)-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole 4-methylbenzenesulfonate (0.38 g, 0.89 mmol) at room temperature 10 minutes, nitrogen protection,Sodium triacetoxyborohydride (0.83 g, 3.93 mmol) was slowly added at 0 C.The reaction was resumed at room temperature for 12 hours.The reaction was quenched by the addition of aqueous ammonia/water (v/v = 2/3, 50 mL) and filtered.The obtained solid was purified by silica gel column chromatography [methanol / dichloromethane (v / v) = 1 / 9]The title compound was obtained (0.30 g, yield 79%).It is a brown foamy solid.

The synthetic route of 951127-25-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ruyuan Yong Xing Technology Services Co., Ltd.; Li Jianhao; Gu Zheng; Deng Xinshan; Tang Wanjun; Zhang Zongyuan; Kang Panpan; Yuan Weihui; Peng Fei; (49 pag.)CN109942583; (2019); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

951127-25-6, tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,951127-25-6

2.46 kg of Compound III and 3.12 kg of Compound II were added to 15 L of N, N-dimethylacetamide, and nitrogenUnder guard,Circulating frozen saline bath to 5 ¡À 5 ,Added dropwise trimethyl orthoformate 2.2Kg,Sodium borohydride acetate was added in portions3.19Kg,Stirred at 5 ¡À 5 C for 2 hours,Heated to 50 ¡À 5 for about 10 hours;Circulating frozen saline bath to 5 ¡À 5 ,45 C below the drop in water 15L,Add Bi temperature at this temperature for 1 hour,Heated to 50 ¡À 5 C for 2 hours,Centrifuge,Wet product washed with water 5L three times,Wet product was added to the water 15L beating 1 hour,Centrifuge,50 C for 12 hours under vacuum.Get gray whiteSolid was added isopropyl ether 12L,Heated to 60 ¡À 5 ,Then add n-heptane 12L, cooled to 15 ¡À 5 , incubated for 1 hour,Suction filtered and dried under vacuum at 40 C for 12 hours to obtain 3.1Kg of white solid with a yield of 82.5%

As the paragraph descriping shows that 951127-25-6 is playing an increasingly important role.

Reference£º
Patent; Shanghai Bozhi Yan Xin Pharmaceutical Co., Ltd.; Ying Shuhuan; Pi Hongjun; Chen Jian; (14 pag.)CN106674227; (2017); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

40191-32-0, Tetrahydro-2H-pyran-4-carbonyl chloride is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

N,O-Dimethylhydroxylamine hydrochloride (1.23 g, 12.7 mmol) and N-methyl morpholine (3.80 mL, 34.5 mmol) were dissolved in DCM (20 mL) and a solution of oxane-4-carbonyl chloride (1.71 g, 11.5 mmol) in DCM (20 mL) was added drop-wise. The reaction mixture was stirred for 2 h, then diluted to 200 mL with DCM, washed with 1 M aq HCl (2*100 mL), 1M aq Na2CO3 (100 mL) and water (100 mL), dried (MgSO4) and concentrated in vacuo to give the crude title compound as a yellow oil (1.87 g, 94%). LCMS (ES+): 174.1 [MH]+.

40191-32-0, The synthetic route of 40191-32-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PROXIMAGEN LIMITED; Evans, David; Carley, Allison; Stewart, Alison; Higginbottom, Michael; Savory, Edward; Simpson, Iain; Nilsson, Marianne; Haraldsson, Martin; Nordling, Erik; Koolmeister, Tobias; US2014/357623; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

220641-87-2, N-Methyltetrahydro-2H-pyran-4-amine is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step a) Intermediate 204 l-(4-Bromophenyl)-N-methyl-N-(tetrahydro-2H-pyran-4-yl)methanesulfonamide To a suspension of N-methyltetrahydro-2H-pyran-4-amine (0.507 g, 4.40 mmol) and sodium carbonate (0.467 g, 4.40 mmol) in MeCN (10 ml) was added (4- bromophenyl)methanesulfonyl chloride (0.593 g, 2.201 mmol) and the reaction mixture was stirred at r.t. for 1.5 h. The mixture was quenched with water and extracted with EtOAc (x 2). The organics were dried (MgS04) and concentrated under reduced pressure to yield l-(4-bromophenyl)-N-methyl-N-(tetrahydro-2H-pyran-4- yl)methanesulfonamide as a white solid (0.634 g, 83 %). ? NMR (400 MHz, MeOD) delta 7.56 (m, 2H, J = 8.34 Hz), 7.38 (m, 2H, J = 8.34 Hz), 4.34 (s, 2H), 3.95 (dd, 2H, J = 1 1.62, 4.55 Hz), 3.69 – 3.82 (m, 1H), 3.35 – 3.43 (m, 2H), 2.72 (s, 3H), 1.74 – 1.87 (m, 2H), 1.45 – 1.53 (m, 2H), 220641-87-2

220641-87-2 N-Methyltetrahydro-2H-pyran-4-amine 6991950, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; RUPRAH, Parminder, Kaur; MERCHANT, Kevin, John; WALSH, Louise, Marie; KERR, Catrina, Morven; FIELDHOUSE, Charlotte; HARRISSON, David; MAINE, Stephanie; HAZEL, Katherine; WO2013/27001; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

125552-89-8, 4-(Bromomethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of N-(2-hydroxyethyl)-4-(2H-tetrazol-5-yl)benzenesulfonamide (200 mg, 0.743 mmol, Intermediate 17) in Lambda/,/V-dimethylformamide (10 ml_), potassium carbonate (205 mg, 1 .485 mmol, commercial source: RCP) was added followed by the addition of 4- (bromomethyl)tetrahydro-2H-pyran (159 mg, 0.88 mmol, commercial source: Aldrich) at 26 C. The reaction mixture was heated to 80 C for 8 h. Upon completion, the reaction mixture was cooled to 26 C and evaporated under reduced pressure. The crude was purified by column chromatography (silicagel 100-200 mesh), eluted with 5% methanol in dichloromethane. The pure fractions were concentrated under reduced pressure to afford N- (2-hydroxyethyl)-4-(2-((tetrahydro-2H-pyran-4-yl)methyl)-2H-tetrazol-5- yl)benzenesulfonamide (80 mg, 18%).1H NMR (400 MHz, DMSO-de) delta 8.28-8.24 (m, 2H), 7.98 (d, J = 8.6 Hz, 2H), 7.79-7.72 (m, 1 H), 4.73-4.65 (m, 3H), 3.88-3.80 (m, 2H), 3.38 (q, J = 6.1 Hz, 2H), 3.29-3.27 (m, 2H), 2.85 (q, J = 5.3 Hz, 2H), 2.35-2.23 (m, 1 H), 1.52-1.46 (m, 2H), 1.40-1.31 (m, 2H). MS m/z [M+H]+= 368.12.

125552-89-8, As the paragraph descriping shows that 125552-89-8 is playing an increasingly important role.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ALEMPARTE-GALLARDO, Carlos; ENCINAS, Lourdes; ESQUIVIAS PROVENCIO, Jorge; (206 pag.)WO2019/34729; (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.23462-75-1,Dihydro-2H-pyran-3(4H)-one,as a common compound, the synthetic route is as follows.

POC13 (3.1 g, 20.0 mmol, 1 eq) was added dropwise to DMF (1.46 g, 20.0 mmol, 1 eq) over 5 minutes at 0C. Dichloromethane (10mL) was added and then the ice-bath was removed. The reaction was kept at 25C for 1 hour, then it was cooled to 0C again. Dihydro-2H-pyran-3(4H)-one 1-4 (2 g, 20.0 mmol, 1 eq) in 5 mL of dichloromethane was added dropwise within 5 minutes. The reaction was kept at 0C for 1 hour. The reaction mixture was quenched by adding 20 mL of sat. NH4C1, and extracted three times with 30 mL of DCM. The combined organic phases were washed with 20 mL of brine,dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (Si02 eluting with a gradient of petroleum ether: ethyl acetate = 50:1 to 20:1) to give 470 mg of compound 1-5 as a yellow oil.

23462-75-1, As the paragraph descriping shows that 23462-75-1 is playing an increasingly important role.

Reference£º
Patent; AQUINNAH PHARMACEUTICALS, INC.; BURNETT, Duane, A.; VACCA, Joseph, P.; (310 pag.)WO2018/119395; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

53911-68-5, 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

53911-68-5, Example 570.5 mmol of an anhydride (1m) was dissolved in 10 mL of methyl t-butyl ether at 20 C., 10 mol % of an organocatalyst (Q-BTBSA) was added thereto, 10 equivalents of methanol was added once thereto, and the mixture was stirred at 20 C. for 1 hours. This reaction was quenched using an aqueous solution of dilute hydrochloric acid (1N, 3 mL). The aqueous layer was extracted with ethyl acetate (2¡Á10 mL), and the combined organic layer was dried with MgSO4 and concentrated. The residue was purified by flash chromatography (25% ethyl acetate in normal-hexane) to obtain a hemiester (1 h, 92% yield). According to the known method (H. Han, Tetrahedron Lett. 2004, 45, 3301-3304), it was determined to obtain an enantiomeric excess of 92% by reacting the hemiester and R-1-(1-naphthyl)ethyl amine to be converted to an ester amide corresponding to the hemiester. The enantioselectivity was measured using high performance liquid chromatography (Kromasil, 90.5:9.5, hexane:isopropyl alcohol, 1 mL/min., t (main product)=9.4 min., t (side product)=17.4 min.).1H NMR (300 MHz, CDCl3) delta 2.56-2.78 (m, 4H), 3.55-3.65 (m, 4H), 7.13-7.16 (m, 2H), 7.24-7.27 (m, 2H); 13C NMR (75 MHz, CDCl3) delta 37.25, 40.00, 40.19, 51.70, 128.56, 128.74, 132.71, 140.63, 171.80, 177.22

As the paragraph descriping shows that 53911-68-5 is playing an increasingly important role.

Reference£º
Patent; SUNGKYUNKWAN UNIVERSITY FOUNDATION FOR CORPORATE COLLABORATION; US2011/213151; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

14774-37-9, Tetrahydropyran-4-methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Prepared as described by adaptation of the following literature reference: Radziszewski, J.G. et al. J. Am. Chem. Soc. 1993, 115, 8401 . To 97 g (810 mmol) of (tetrahydro-pyran-4-yl)-methanol in 2- methyltetrahydrofuran (190 mL) are added 165 mL of 50% aq. 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 18h. The suspension is poured into a mixture of ice-water (280 mL) and aq. HCI 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 toluene-4-sulfonic acid tetrahydro-pyran-4-ylmethyl ester. Yield: 99%; ESI-MS: 271 [M+H]+

14774-37-9, The synthetic route of 14774-37-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; BINDER, Florian; DOODS, Henri; MUELLER, Stephan, Georg; NICHOLSON, Janet, Rachel; SAUER, Achim; WO2014/184327; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics