Category: Tetrahydropyrans

344329-76-6, Tetrahydro-2H-pyran-4-carboxamide is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A mixture of bromo-ketone (0.6 g,2.9 mmol), amide (0.55 g, 3.6 mmol, 1.25 equiv), and silver triflate (0.9 g,3.6 mmol, 1.25 equiv) in ethyl acetate (4 mL) was heated to 50?70 ¡ãC. After thereaction was deemed complete by HPLC analysis, the mixture was cooled to 20 ¡ãC and diluted with ethyl acetate (3 mL). A solution of sat?d NaCl (3?4 mL)was added and the mixture stirred at 20 ¡ãC for at least 4 h. The silver salts (AgBr and AgCl) are removed by filtration and the resulting biphasic solution transferred to a separatory funnel and the layers separated. The organic layer isthen washed with water (4 mL), 5percent NaHCO3 (4 mL), 1 N HCl (4 mL), and water(4 mL). The organic layer is concentrated to dryness and the residue purified by flash column chromatography (5percent EtOAc/hexanes) to obtain pure oxazole product.

344329-76-6 Tetrahydro-2H-pyran-4-carboxamide 13197203, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Article; Bailey, Jessica L.; Sudini, Ravinder R.; Tetrahedron Letters; vol. 55; 27; (2014); p. 3674 – 3677;,
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.40191-32-0,Tetrahydro-2H-pyran-4-carbonyl chloride,as a common compound, the synthetic route is as follows.

The compound, Methyl (2S)-2-amino-3-{N-[4-(4-trifluoromethylphenoxy)phenyl]-N-methanesulfonylamino}propionate, was prepared from 4-(4-trifluoromethylphenoxy)aniline in accordance with the sequence of general procedure I, II, III, and IV (GP-I, GP-II, GP-III, and GP-IV) as described herein above for reference examples. To a solution of Methyl (2S)-2-amino-3-{N-[4-(4-trifluoromethylphenoxy)phenyl]-N-methanesulfonylamino}propionate (86 mg, 0.2 mmol) in CH2Cl2/THF (1.5 mL/1.5 mL) was added 2,6-lutidine (0.1 mL, 1.2 mmol) and then 4-tetropyranecarboxyl chloride (119 mg, 0.8 mmol) at 0 C. The mixture was allowed to warm to rt and stirred for 1 h. The mixture was poured into Et2O/H2O (100 mL/100 mL) and HCl(aq) (2 N, 5 mL) was added. The organic was washed with NaOH(aq) (10%, 10 mL), H2O (40 mL), brine (50 mL), dried (Na2SO4), and filtered. After removal of solvent, the product was dried in vacuo to give 102 mg of Methyl (2S)-2-[(tetrahydropyran-4-yl)carbonylamino]-3-{N-[4-(4-trifluoromethylphenoxy)phenyl]-N-methanesulfonylamino}propionate (94%) as a white solid. 1H NMR (300 MHz, CDCl3) delta 7.62 (d, J=9.0 Hz, 2H), 7.33 (d, J=9.0 Hz, 2H), 7.12-7.05 (m, 4H), 6.45 (d, J=9.0 Hz, 1H), 4.68-4.62 (m, 1H), 4.17-3.98 (m, 4H), 3.59 (s, 3H), 3.47-3.38 (m, 2H), 2.90 (s, 3H), 2.42-2.35 (m, 1H), 1.80-1.76 (m, 4H); MS (EI, m/z): 545 (M++1, 100).

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

Reference£º
Patent; YANG, Shyh-Ming; Wang, Bingbing; Scannevin, Robert; Rhodes, Kenneth; Lagu, Bharat; Wilson, Lawrence J.; Karnachi, Prabha; Murray, William V.; US2008/85893; (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.4295-99-2,4-Cyanotetrahydro-4H-pyran,as a common compound, the synthetic route is as follows.

To a solution of tetrahydro-2H-pyran-4-carbonitrile (2.15 g, 19.34 mmol) in dry THE (15 mL) cooled at -78 C, LiHDMS solution (1M in THE, 24.2 mL, 24.2 mmol) was added dropwise under nitrogen atmosphere and the mixture was stirred at this temperature for lh. Then, a solution of (3-iodopropoxy)methylbenzene (6.14 g, 22.2 mmol) in dry THE (10 mL) was added and the reaction mixture was allowed to reachrt and stirred overnight. The solvent was evaporated and the residue was diluted with water and Et20. The phases were separated and the aqueous phase was extracted several times with Et20. The organic phases were combined and washed with water and brine, the solvent was evaporated and the residue thus obtained was purified by flash chromatography on silica gel, gradient CH to CH:AcOEt (80:20) to give the titlecompound (4.35 g, 87% yield).HPLC-MS (Method B): Ret, 2.28 mm; ESI+-MS mlz, 260.31 (M+H).

As the paragraph descriping shows that 4295-99-2 is playing an increasingly important role.

Reference£º
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; GARCIA-LOPEZ, Monica; ALMANSA-ROSALES, Carmen; (168 pag.)WO2018/108319; (2018); 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 the stirred solution of lH-indole-2-carbaldehyde (1, 1.0 g, 6.89 mmol) in N, N-dimethylformamide (10 mL), cesium carbonate (6.70 g, 20.68 mmol) and 4- (bromomethyl)tetrahydro-2H-pyran (1.48 g, 8.27 mmol) were added at room temperature. The reaction mixture was stirred at room temperature for 1 h. After completion of reaction, reaction mixture was diluted with water and extracted with ethyl acetate (200 mL x 2). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude was purified by CombiFlash using 12 g RediSep and 5% ethyl acetate in hexane as eluent to afford l-((tetrahydro-2H-pyran-4-yl)methyl)-lH-indole-2-carbaldehyde as white solid). Yield: 0.80 g (48%). MS (ESI);243.13 m/z found: 244.17[M+H]+1.

125552-89-8 4-(Bromomethyl)tetrahydropyran 2773286, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; JUBILANT BIOSYS LIMITED; HALLUR, Gurulingappa; DURAISWAMY, Athisayamani Jeyaraj; PURRA, Buchi Reddy; RAO, N.V.S.K.; RAJAGOPAL, Sridharan; (247 pag.)WO2019/58393; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

31608-22-7, 2-(4-Bromobutoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2-[4-(2,3-Difluorophenoxy)butoxy]-tetrahydropyran (20) To a solution of 2-(4-bromobutoxy)-tetrahydropyran (18) (1 equi.) and commercially available 2,3-difluorophenol (19) (1 equi.) in DMF (3 mL/mmole), cesium carbonate (1.25 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h, quenched with water, extracted with ethyl acetate:hexane (1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (5% EtOAc/hexanes) and recrystallization from acetonitrile gave 2-[4-(2,3-difluorophenoxy)-butoxy]-tetrahydropyran(20), as a white solid (84%).

31608-22-7 2-(4-Bromobutoxy)tetrahydro-2H-pyran 559019, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Wand, Michael; Gough, Neil; Chen, Xin Hua; US2003/17278; (2003); 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

Example 10; 1-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-4-{4-[methyl-(tetrahydro-pyran-4-yl)-amino]-butyl}-[1,4]diazepan-5-one; 1-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-4-{4-[methyl-(tetrahydro-pyran-4-yl)-amino]-butyl}-[1,4]diazepan-5-one; A solution of 0.100 g (0.20 mmol) of 1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-4-(4-iodo-butyl)-[1,4]diazepan-5-one (example 9B) in 3.1 ml of DMA was treated with free methyl-(tetrahydro-pyran-4-yl)-amine in 1 ml of toluene [0.035 g (0.22 mmol) methyl-(tetrahydro-pyran-4-yl)-amine hydrochloride were dissolved in 0.8 ml of 0.5 N NaOH was extracted with toluene (2 ml). The organic phase was dried over Na2SO4] and stirred for 22 h at RT, 0.06 ml (0.40 mmol) of Et3N was added and stirring was continued for 18 h at 50 C. Again methyl-(tetrahydro-pyran-4-yl)-amine in 1 ml of CH2Cl2 [0.035 g (0.22 mmol) methyl-(tetrahydro-pyran-4-yl)-amine hydrochloridewere dissolved in 0.5 ml aqueous 10% NaCl solution/0.4 ml of 1 N NaOH was extracted with CH2Cl2 (1 ml). The organic phase was dried over Na2SO4] was added and heated for 9 h at 50 C. The reaction was extracted with aqueous saturated NaHCO3/Et2O (3¡Á). The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4), concentrated and evaporated. Purification by catridges, Si-Amine, 70 ml, 20 g (n-heptane/EtOAc 1:4 to 1:9) gave 0.004 g (4%) of the title compound as a light yellow semisolid. MS: 482.3 (MH+, 2Cl).

The synthetic route of 220641-87-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Aebi, Johannes; Green, Luke; Mattei, Patrizio; Ricklin, Fabienne; Roche, Olivier; Zahm, Peter; US2007/249589; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

33821-94-2, 2-(3-Bromopropoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Potassium hydride (30% w/w in mineral oil, 2.2 g, 16.5 mmol) was suspended in 1 ,2- dimethoxyethane (20.0 mL) and the suspension cooled to 0-5C (ice bath). A solution of 2- methyl-2-(methylsulfonimidoyl)propanenitrile (Int-5, 2.0 g, 13.7 mmol) in 1 ,2-dimethoxyethane (15 mL) was added dropwise over 10 min. The ice bath was removed and the mixture was stirred for 3 h at room temperature. After that, it was cooled again to 0-5C and tetrabutylammonium bromide (235 mg, 730 muiotaetaomicron) followed by 2-(3-bromopropoxy)tetrahydro-2H-pyran (Int-6, 3.95 g, 3.00 mL, 17.7 mmol) was added. The reaction mixture was stirred for 16 h at room temperature. Then, the mixture was poured onto a saturated aqueous solution of sodium hydrogencarbonate (60 mL) and diluted with ethyl acetate (180 mL). After phase separation, the aqueous phase was extraced with ethyl acetate (2 x 50 mL), the combined organic extracts were dried (sodium sulfate) and concentrated in vacuo to afford a yellow biphasic oil as crude product. This was purified by column chromatography (silica gel, 100 g, eluting with ethyl acetate / n- heptane, gradient 40:60 to 100:0) to yield, after drying in vacuo (50C, 5 mbar), the title compound as mixture of diastereoisomers as a colorless viscous oil (3.28 g, 83%). HPLC (method LCMS_gradient) tR = 1.6 min. 1H NMR (CDC13, 400 MHz): delta 1.47-1.60 (m, 4 H), 1.68- 1.77 (m, 1 H), 1.76 (br s, 6 H), 1.78-1.88 (m, 3 H), 3.06 & 3.07 (2s, 3 H, dias ), 3.20-3.41 (m, 2 H), 3.45-3.54 (m, 2 H), 3.79-3.91 (m, 2 H), 4.56-4.60 (m, 1 H). MS (ES+) m/z 205.1 [M+H- (CsHgO)] .

The synthetic route of 33821-94-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; CUENI, Philipp; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; KUGLSTATTER, Andreas; OBST SANDER, Ulrike; PETERS, Jens-Uwe; ROGERS-EVANS, Mark; VIFIAN, Walter; WOLTERING, Thomas; (231 pag.)WO2016/55496; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

3301-94-8, 6-Butyltetrahydro-2H-pyran-2-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of diisopropylamine (1.21 ml, 8.63 mmol) in THF (tetrahydrofuran) (33 ml) was cooled to -78C under a nitrogen atmosphere, to which a butyllithium-hexane solution (1.1 M, 7.27 ml, 8.00 mmol) was added, and 10 minutes later, a solution of 6-butyltetrahydro-2H-pyran-2-one (1.00 g, 6.40 mmol) in THF (2 ml) was dropped, and stirred for 10 minutes. Subsequently, a solution of phenylselenyl chloride (1.19 g, 6.21 mmol) in THF (5 ml) was slowly dropped, and stirred at -78C for another 30 minutes, to which a saturated ammonium chloride solution was dropped to terminate the reaction. The reaction mixture was extracted with hexane, and its organic layer was dried with anhydrous sodium sulfate and distilled off under reduced pressure. The residue was purified by a silica gel column chromatography (hexane-ethyl acetate 10:1-8:1-6:1) so as to obtain a pure phenylselenide (842 mg, 42%) as a diastereomer mixture.

3301-94-8 6-Butyltetrahydro-2H-pyran-2-one 18698, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Tsujimoto Chemical Co., Ltd.; Iinuma, Munekazu; IINUMA, Munekazu; EP2832732; (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.72886-97-6,(S)-Tetrahydro-2H-pyran-3-ol,as a common compound, the synthetic route is as follows.

To a solution of (S)-tetrahydro-2H-pyran-3-ol (compound 3) (51.0 mg, 0.50 mmol) in CH2Cl2 (2.5 mL) was added with Et3N (55 mg, 0.55 mmol) and DMAP (3.0 mg, 0.025 mmol), followed by the addition of cinnamoyl chloride (92.0 mg, 0.55 mmol) at 0 C. The mixture was stirred for 18 h then added with saturated NaHCO3 solution. The organic phase was separated and washed with brine, dried with anhydrous Na2SO4. The crude product was purified via silica gel column with PE/EtOAc (30:1-10:1) to give the title compound 4 as white foam

The synthetic route of 72886-97-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Geng, Yang; Zheng, Maolin; Li, Jingya; Zou, Dapeng; Wu, Yusheng; Wu, Yangjie; Tetrahedron Letters; vol. 58; 42; (2017); p. 3966 – 3969;,
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.101691-94-5,4-(Iodomethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

Under argon, 1.31 ml of 1,1,1,3,3,3-hexamethyldisilazane are dissolved in 20 ml of tetrahydrofuran. With ice cooling, 2.3 ml of n-butyllithium (2.5 M in n-hexane) are added dropwise, and the mixture is stirred at 0 C. for another 30 minutes. At -78 C., this solution is then added dropwise to a stirred solution of 2.0 g of tert-butyl 2-ethoxycarbonylmethyl-5,5-dioxo-5H-phenothiazine-10-carboxylate in 100 ml of tetrahydrofuran. The reaction mixture is stirred at -78 C. for 20 minutes, and 1.1 g of 4-(iodomethyl)tetrahydro-2H-pyran are then added dropwise. The cooling bath is removed and the mixture is allowed to slowly warm to room temperature. The reaction mixture is stirred at room temperature overnight. 10 ml of water are then added, the tetrahydrofuran is removed under reduced pressure and the residue is extracted three times with in each case 100 ml of ethyl acetate. The combined organic phases are dried over MgSO4 and then concentrated under reduced pressure. The residue is purified on silica gel using the mobile phase n-heptane:ethyl acetate (100%:0%)=>n-heptane:ethyl acetate (50%:50%). This gives 700 mg of tert-butyl 2-[1-ethoxycarbonyl-2-(tetrahydropyran-4-yl)ethyl]-5,5-dioxo-5H-phenothiazine-10-carboxylate. C27H33NO7S (515.63), LCMS (ESI): 533.2 (M+NH4+), 460.1 (M-tert-butyl+H+), Rf (n-heptane:EA=1:1)=0.28.

As the paragraph descriping shows that 101691-94-5 is playing an increasingly important role.

Reference£º
Patent; SANOFI-AVENTIS; US2009/325942; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics