Heterocyclic Building Blocks-Tetrahydropyrans

2081-44-9, Tetrahydro-2H-pyran-4-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 95A (enantiomer 1)Step I: tetrahydro-2H-pyran-4-yl methanesulfonate; P At r.L to a solution of tetrahydro-4H-pyran-4-ol (90 uL, . mmol; Aldrich, Cat. No. 198234) in methylene chloride (3 mL) was added methanesulfonyl chloride (91 uL, 1.2 mmol), followed by triethylamine (0.20 mL, 1.5 mmol) and 4-dimethylaminopyridine (12 mg, 0.098 mmol). The mixture was stirred at r.L for 3 h. It was diluted with methylene chloride. The solution was washed with water and brine, dried over l^SCv After filtration, the filtrate was concentrated to yield 0.21 g of the product (crude) which was directly used in the next step reaction without further purification., 2081-44-9

As the paragraph descriping shows that 2081-44-9 is playing an increasingly important role.

Reference£º
Patent; INCYTE CORPORATION; ZHANG, Colin; QIAN, Ding-quan; ZHUO, Jincong; YAO, Wenqing; WO2010/75270; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

85064-61-5,85064-61-5, Tetrahydropyranyl-4-acetic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

a) N-{2-r(2S,5R)-5-r4-(3-Methoxypropyl)-3,4-dihvdro-2H-benzopi ,41oxazin-6- ylmethoxyi-1 -(toluene-4-sulphonyl)piperidin-2-yl1-1 ,1 -dimethylethyl)-2-(tetrahvdro- pyran-4-yl)acetamide; A solution of 0.511 mmol of tetrahydropyranyl-4-acetic acid [85064-61-5] in 5 ml of dichloromethane is treated with 1.023 mmol of 1 -chloro-N,N-2-thmethylpropenyl- amine. The reaction mixture is stirred at room temperature for 1.5 hours. In a second flask, a solution of 0.341 mmol of 2-[(2S,5R)-5-[4-(3-methoxypropyl)-3,4-dihydro-2H- benzo[1 ,4]oxazin-6-ylmethoxy]-1 -(toluene-4-sulphonyl)piperidin-2-yl]-1 ,1 -dimethyl- ethylamine in 10 ml of dichloromethane are treated with 1.023 mmol of thethylamine, and cooled to 00C. The solution of acid chloride is added dropwise to this second flask, and the reaction mixture is stirred at room temperature for 2 hours. Water is added, and the aqueous phase is extracted with dichloromethane (3X). The combined organic extracts are dried over sodium sulphate, concentrated and purified by flash chromatography (SiO2 60F) to afford the title compound as a dark yellow resin. Rf = 0.20 (dichloromethane-methanol-conc ammonia); Rt = 4.94 (gradient I).

The synthetic route of 85064-61-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVARTIS AG; WO2009/106599; (2009); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

4677-20-7, 4-(2-Bromoethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A mixture of 4 (0.054g, 0.20mmol), K2CO3 (0.11g, 0.8mmol), DMF (2.0mL), and 2-bromoethanol (0.038g, 0.30mmol) in a 10mL microwave tube was heated under microwave irradiation at 150C for 10min. After cooling to room temperature, (4-(N-methylsulfamoyl)phenyl)boronic acid (0.065g, 0.30mmol), Pd(PPh3)4 (0.023g, 0.020mmol), and H2O (1.0mL) were added sequentially. The resulting mixture was stirred at room temperature for 1.0min and then heated under microwave irradiation at 150C for 15min. After cooling to room temperature, the mixture was quenched with H2O and extracted with EtOAc (3¡Á). The combined organic layers were dried (Na2SO4) and concentrated. The residue was purified by an ISCO silica gel column to provide the title compound 12 (0.044g, 57%) as a white solid.

4677-20-7, The synthetic route of 4677-20-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Liu, Jing; Zhang, Weihe; Stashko, Michael A.; DeRyckere, Deborah; Cummings, Christopher T.; Hunter, Debra; Yang, Chao; Jayakody, Chatura N.; Cheng, Nancy; Simpson, Catherine; Norris-Drouin, Jacqueline; Sather, Susan; Kireev, Dmitri; Janzen, William P.; Earp, H. Shelton; Graham, Douglas K.; Frye, Stephen V.; Wang, Xiaodong; European Journal of Medicinal Chemistry; vol. 65; (2013); p. 83 – 93;,
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.

To a solution of (tetrahydropyran-3-yl)-methanol (Matrix, 1.67 g, 14.4 mmol) in 15 mL of CH2Cl2 and 15 mL of pyridine was added p- toluenesulfonyl chloride (2.9 g, 15.1 mmol) in portions over 10 minutes. The mixture stirred at ambient temperature for 18 hours and was quenched with 10 mL of saturated, aqueous NaHCCh. The layers were separated and the aqueous phase was extracted three 5 mL of portions OfCH2Cl2. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification via column chromatography (SiO2, 70% hexanes in ethyl acetate) afforded the title compound. MS (DCI/NH3) m/z 288 (M+NH4)+, 14774-36-8

The synthetic route of 14774-36-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ABBOTT LABORATORIES; WO2009/67613; (2009); 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.

Intermediate 18A (4-Amino-5-bromopyrrolo[2,l-fj[l ,2,4]triazin-7-yl)(tetrahydro-2/ -pyran-4-yl)methanol In a 50 l. three-necked flask equipped with a condenser, a thermometer and a dropping funnel, which was purged with argon, a Gri uard reagent was prepared from magnesium turnings (484 mg, 19.9 mmol) and 4-chlorotetrahydropyrane (2.4 g, 19.9 mmol) in dry THF (14 mL). To this solution was added at 0C a suspension of Intermediate 16A (1.2 g, 3.98 mmol) in THF (20 mL), and the reaction mixture was allowed to stir for 1 h at room temperature. It was then quenched with saturated aqueous ammonium chloride solution and extracted with ethyl acetate (2 x 50 mL). The organic layer was washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by preparative HPLC (method 3). Yield: 0.5 g (38% of th.). LC-MS (method 6): R, = 0.66 min; MS (ESIpos): m/z (%) = 327.0 (100) [M+H]+, MS (ESIneg): m/z (%) = 325.1 (100) [M-H]~

1768-64-5, 1768-64-5 4-Chlorotetrahydropyran 137202, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Bayer Pharma Aktiengesellschaft; KLAR, Juergen; VOEHRINGER, Verena; TELSER, Joachim; LOBELL, Mario; SUessMEIER, Frank; LI, Volkhart Min-Jian; BOeTTGER, Michael; GOLZ, Stefan; LANG, Dieter; SCHLEMMER, Karl-Heinz; SCHLANGE, Thomas; SCHALL, Andreas; FU, Wenlang; WO2013/4551; (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.2081-44-9,Tetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

Step 2: Synthesis of Compound A3To a solution of 133 g (1.31 mol) of compound A2 in pyridine (1.5 L) are added 373 g (1.95 mol) of p-toluenesulfonylchloride portionwise at 10 C. After complete addition the reaction is allowed to warm to room temperature and stirred for 18 h. The reaction is poured onto a stirred mixture of aqueous HCl/ice. The resulting precipitate is isolated by filtration and dissolved in DCM (1 L). The organic layer is washed with 1M aqueous HC1 solution (1 L), followed by saturated aqueous NaHCC>3 solution (1 L) and is then dried over Na2S04. Filtration and concentration of the filtrate under reduced pressure gives 300 g of compound A3 as an orange oil. Yield: 90%, ES-MS: m/z: 257 [M+H], 279 [M+Na]

2081-44-9, The synthetic route of 2081-44-9 has been constantly updated, and we look forward to future research findings.

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.103260-44-2,Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate,as a common compound, the synthetic route is as follows.

To a solution of (Tetrahydro-pyran-4-yl)-acetic acid ethyl ester (2.0 g, 11.6 mmol) in 50 mL of THF at -78 C. LDA (1.0 M, 17.4 mL, 34.8 mmol) is added dropwise. The solution is stirred for 0.5 h and treated with HMPA (3.2 mL, 9.3 mmol) and MeI (4.94 g, 34.8 mmol). The reaction mixture is stirred at the same temperature for 0.5 h and for 1.5 h at 0 C., acidified with aqueous 1 N aqueous HCl solution, and extracted twice with ether (2¡Á40 mL). The organic phase is washed with saturated aqueous NaCl solution, dried (MgSO4), and concentrated in vacuo to give 1.8 g of 2-(Tetrahydro-pyran-4-yl)-propionic acid ethyl ester which is hydrolyzed without further purification., 103260-44-2

The synthetic route of 103260-44-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Breitenstein, Werner; Erhardt, Claus; Maibaum, Juergen Klaus; Ostermann, Nils; Zimmermann, Juerg; Masuya, Keiichi; Konishi, Kazuhide; Yokokawa, Fumiaki; Kanazawa, Takanori; Jacoby, Edgar; Marzinzik, Andreas; Grosche, Philipp; Kawakami, Shimpei; US2009/233920; (2009); 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

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

To 5.00 g (43.0 mmol) of (tetrahydro-pyran-yl)-methanol in DCM (50 mL) are added 67 mg of 2,2,6,6-tetramethyl-1-piperidinyloxy (0.43 mmol), a solution of 9.04 g (108 mmol) NaHCO3 in water (70 mL) and 512 mg (4.30 mmol) of potassium bromide at 20 C. The suspension is cooled in an ice bath to 4 C. Then a solution of 23.5 mL sodium hypochlorite (10-15% free chlorine; 47.4 mmol) is added in 35 min. The suspension is stirred for 30 min at 4-9 C. and further 45 min to reach 17 C. 4.80 mL sodium hypochlorite (10-15% free chlorine) is added within 15 min. The reaction is stirred for 16 h at RT. The suspension is filtered and the layers are separated. The aq. layer is washed with 50 mL DCM, the combined organic layers are washed with 50 mL water. The solvent is removed under reduced pressure to afford 3.00 g of tetrahydro-pyran-4-carbaldehyde. Yield: 61%; ESI-MS: 113 [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 Paul Christian; Doods, Henri; Mueller, Stephan Georg; Nicholson, Janet Rachel; Sauer, Achim; US8865744; (2014); B1;,
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

A solution of the product from step a (9.Og, 41.4mmol) and NEt3 (12.73mL, 91.1mmol) in DCM (30OmL) was added dropwise to a solution of triphosgene (4.06g, 13.7mmol) in DCM(16OmL) at -4O0C. The reaction mixture was stirred at this temperature for 20min whereupon a solution of the product from step b (8.97g, 41.4mmol) in DCM (16OmL) was added dropwise.The reaction mixture was allowed to warm to ambient temperature and was washed with H2O(40OmL), saturated NaHCO3 (40OmL), brine (40OmL) and dried (MgSO4). The residue, obtained following filtration and evaporation, was dissolved in DCM (5OmL) and TFA (5OmL) and stirred for lhr. The mixture was evaporated to dryness and the residue dissolved in DCM(10OmL), washed with 10% aqueous K2CO3 (10OmL), and dried (MgSO4). Filtration and evaporation of the solvent afforded the product (13.47g, 95%). 1H NMR (CDCl3) 7.25-6.38(4H, m), 4.15 (IH, m), 4.02 (2H, m), 3.48 (2H, m), 2.70 (IH, m), 2.33 (3H, s), 2.25-1.25 (14H, m), 693287-79-5

The synthetic route of 693287-79-5 has been constantly updated, and we look forward to future research findings.

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