Heterocyclic Building Blocks-Tetrahydropyrans

127956-11-0, Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Into a 250-mL round-bottom flask, was placed a mixture of methyl 4-oxo-tetrahydro-2H- pyran-3-carhoxylate (564 g, 3569 mmoi, 100 eq.), toluene (100 mL), ethane-1,2-diol (4.43g. 71.39mmol, 2.0 eq.),p.-TsOH (615 mg. 3.57 mmol, 0.10 eq.). The resulting mixture was allowed to stir for24 h with refiux under a dean stark trap. The mixture was concentrated and the residue was puiitied by a silica gel column eluted with 20%ethyl acetate/petroleum ether to afford methyl 1,4,8- trioxaspiro[4.5]decane-6-carboxylate as a colorless oil (6.7 g, 93%). LCMS (ES) [M+1] m/z 203.1.

As the paragraph descriping shows that 127956-11-0 is playing an increasingly important role.

Reference£º
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; YU, Ming; LI, Zhe; (206 pag.)WO2018/119208; (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.1197-66-6,2,2,6,6-Tetramethyl-2H-3,5,6-trihydropyran-4-one,as a common compound, the synthetic route is as follows.

Zinc powder (5.20g, 80mmol) in 100mL of tetrahydrofuran was added, was added titanium tetrachloride (4.4mL, 40mmol), the reaction was refluxed for 2 hours, cooled to 0 deg.] C, was added lithium tetrahydroaluminate (750mg, 20mmol),The mixture was stirred under ice bath for 10 minutes. Triethylamine (2.8 mL, 20 mmol) was added and the reaction was refluxed for 1 hour. The prefabricated 10 mL(4-bromophenyl) (3-fluoro-1- (tetrahydro-2H-pyran-2-yl) -1H-indazol-5-yl) methanone4c (2.02 g, 5 mmol) and2,2,6,6-tetramethyldihydro-2H-pyran-4 (3H) -one(2.34 g, 15 mmol) in tetrahydrofuran was refluxed for 1 hour. After completion of the reaction, the reaction was quenched by the addition of 50 mL of water, extracted with ethyl acetate (50 mL x 3) and the organic phase was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography eluting with eluent system B to give the title product5-(4-bromophenyl) methyl) -3-fluoro-1- (tetrahydro-2H-pyran-2-yl) -1H-indazole12a (2.35 g, yellow viscous) in 89% yield.

As the paragraph descriping shows that 1197-66-6 is playing an increasingly important role.

Reference£º
Patent; Yang, Fanglong; Wang, Chunfei; Wang, Yang; He, Mingxun; Hu, Qiyue; He, Feng; Jiangsu Hengrui Pharmaceutical Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; (53 pag.)CN106518768; (2017); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

103260-44-2, Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a suspension of lithium aluminium hydride (11 g, 0.29 mol) in dry tetrahydrofuran (350 mL) at 0 C. was added a solution of (tetrahydro-pyran-4-yl)-acetic acid ethyl ester (25 g, 0.145 mol) in dry tetrahydrofuran (100 mL) dropwise. The resulting mixture was then refluxed for 16 h. After cooling to 0 C., the reaction mixture was quenched carefully by slow addition of a saturated sodium carbonate solution (50 mL). The mixture was decanted and the precipitate was washed with tetrahydrofuran (2¡Á200 mL). The combined tetrahydrofuran layers were dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-(tetrahydro-pyran-4-yl)-ethanol (13 g, 69%) as a yellow oil which was used in the next step without purification.

As the paragraph descriping shows that 103260-44-2 is playing an increasingly important role.

Reference£º
Patent; Berthel, Steven Joseph; Chen, Li; Corbett, Wendy Lea; Feng, LiChun; Haynes, Nancy-Ellen; Kester, Robert Francis; So, Sung-Sau; Tilley, Jefferson Wright; US2011/144105; (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.101691-65-0,(Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

[0217] A solution of (tetrahydro-pyran-4-yl)-methanol (1.0 g, 8.61 mmol, prepared according to WO 99/00385) in methylene chloride (30 mL) at 25 C. was treated with 4-(dimethylamino)pyridine (1.17 g, 9.47 mmol) and p-toluenesulfonyl chloride (1.64 g, 8.61 mmol) and then was allowed to stir at 25 C. overnight. The reaction was then transferred to a separatory funnel and washed with a 1N aqueous hydrochloric acid solution (10 mL), a saturated aqueous sodium bicarbonate solution (10 mL), and a saturated aqueous sodium chloride solution (10 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 75/25 hexanes/ethyl acetate) afforded toluene-4-sulfonic acid tetrahydro-pyran-4-yl methyl ester (1.77 g, 76%) as a colorless oil. [0218] A solution of toluene-4-sulfonic acid tetrahydro-pyran-4-yl methyl ester (1.77 g, 6.55 mmol) and sodium iodide (2.85 g, 18.99 mmol) in acetone (26 mL) was heated to 60 C. for 16 h. The resulting suspension was then cooled to 10 C. and filtered. The salts were rinsed with cold acetone (5 mL), and the filtrate and washings were concentrated in vacuo to a thick slurry. This slurry was treated with methylene chloride (10 mL). The resulting precipitate was removed by filtration and was washed with methylene chloride (10 mL). The filtrate and washings were then dried over magnesium sulfate, filtered through a pad of silica gel, and then concentrated in vacuo to afford 4-iodomethyl-tetrahydro-pyran as a light yellow oil. [0219] A solution of diisopropylamine (0.33 mL, 2.38 mmol) in tetrahydrofuran (6 mL) cooled to -78 C. under an argon atmosphere was treated with a 2.5M solution of n-butyllithium in hexanes (0.95 mL, 2.38 mmol). The reaction mixture was stirred at -78 C. for 15 min, after which time, a solution of (3-chloro-4-methylsulfanyl-phenyl)-acetic acid methyl ester (prepared as in Example 4, 500 mg, 2.17 mmol) in tetrahydrofuran (1 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (0.5 mL) was slowly added via a cannula. The greenish yellow solution was allowed to stir at -78 C. for 1 h, after which time, a solution of 4-iodomethyl-tetrahydro-pyran (588 mg, 2.60 mmol) in 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (0.5 mL) was added via a cannula. The reaction mixture was then allowed to warm to 25 C., where it was stirred for 16 h. The reaction mixture was then quenched by the addition of a saturated aqueous ammonium chloride solution (30 mL). This solution was extracted with ethyl acetate (3¡Á20 mL). The combined organic layers were washed with a 10% aqueous sulfuric acid solution (2¡Á50 mL) and a saturated aqueous sodium bicarbonate solution (2¡Á50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 75/25 hexanes/ethyl acetate) afforded 2-(3-chloro-4-methylsulfanyl-phenyl)-3-(tetrahydro-pyran-4-yl)-propionic acid methyl ester (431 mg, 61%) as a yellow oil: EI-HRMS m/e calcd for C16H21ClO3S (M+) 328.0900, found 328.0898. [0220] A solution of 2-(3-chloro-4-methylsulfanyl-phenyl)-3-(tetrahydro-pyran-4-yl)-propionic acid methyl ester (200 mg, 0.61 mmol) in formic acid (0.23 mL) and tetrahydrofuran (0.5 mL) cooled to 0 C. was treated with a 30% aqueous hydrogen peroxide solution (0.35 mL, 3.04 mmol). The reaction was slowly warmed to 25 C. where it was stirred for 16 h. The reaction mixture was then cooled to 0 C., quenched with a saturated aqueous sodium sulfite solution, and then extracted with ethyl acetate (3¡Á20 mL). The organics were dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 12M, Silica, 60/40 hexanes/ethyl acetate) afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-3-(tetrahydro-pyran-4-yl)-propionic acid methyl ester (190 mg, 87%) as a colorless oil: (ES)+-HRMS m/e calcd for C16H21ClO5S (M+Na)+ 383.0690, found 383.0692. [0221] A

As the paragraph descriping shows that 101691-65-0 is playing an increasingly important role.

Reference£º
Patent; Corbett, Wendy Lea; Grimsby, Joseph Samuel; Haynes, Nancy-Ellen; Kester, Robert Francis; Mahaney, Paige Erin; Racha, Jagdish Kumar; Sarabu, Ramakanth; Wang, Ka; US2003/225283; (2003); 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.

Step 6: Ru Oxidation to Provide 9; To a solution of the alcohol 8 (40.0 g, 121.4 mmol) in CH3CN (120 mL), AcOH (20 mL), and H2O (20 mL) was added a solution of RuCl3 (50.4 mg, 0.243 mmol) in H2O (40 mL) at 0 C. NaBrO3 (9.2 g, 60.7 mmol) was added in portions at 0 C. The resulting reaction mixture was stirred at 0 C. until a complete consumption of alcohol 8 was achieved by HPLC. H2O (600 mL) was added dropwise over 5 h at 0 C. The slurry was aged overnight at 0 C. The product was collected by filtration, washed with CH3CN/H2O=1/9 (200 mL¡Á2), and dried under vacuum to give 9. 9 has two rotomers in DMSO in about a 4:1 ratio at ambient temperature. For the major rotomer of 9: 1H NMR (500 MHz, DMSO-d6): delta 7.27 (m, 1H), 7.20 (m, 2H), 7.12 (d, J=9.2 Hz, 1H), 4.76 (d, J=9.5 Hz, 1H), 4.19 (d, J=16.1H), 4.10 (d, J=16.1 z, 1H), 4.05 (m, 1H), 2.76 (dd, J=16.4, 6.2 Hz, 1H), 2.71 (dd, J=16.4, 10.1 Hz, 1H), 1.20 (s, 9H). 13C-NMR (125 MHz, d6-DMSO): delta 205.4, 158.0 (d, J=236.9 Hz), 156.2 (dd, J=241.8, 1.8 Hz), 154.2, 127.8 (dd, J=16.0, 8.0 Hz), 116.6 (dd, J=25.2, 8.0 Hz), 116.2 (dd, J=23.4, 8.0 Hz), 115.2 (dd, J=24.0, 3.1 Hz), 77.9, 74.5, 73.6, 50.6, 44.1, 27.9.

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

Reference£º
Patent; Xu, Feng; Kim, Mary M.; Kohmura, Yoshinori; Sladicka, Tricia; Rosen, Jonathan D.; Zacuto, Michael J.; US2009/187028; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

5631-96-9, 2-(2-Chloroethoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A reaction vessel is charged with tert-butyl 3-(4-hydroxyphenyl)-2,6-dioxopiperidine-1- carboxylate (1 equiv.), potassium carbonate (2 equiv.) and DMF (0.5 M). 2-(2- Chloroethoxy)tetrahydro-2H-pyran (1.1 equiv.) is added and the reaction is heated at 110 C for 12 hours. The reaction is then cooled to ambient temperature and concentrated. The residue is taken up in water and ethyl acetate and the layers separated. The aqueous layer is extracted with ethyl acetate (2x). The combined organic layer is washed with brine, dried over sodium sulfate, filtered and concentrated. The crude residue is used directly in the following reaction.

5631-96-9 2-(2-Chloroethoxy)tetrahydro-2H-pyran 254951, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); A1;,
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

Intermediate 23Tetrahydro-2H-pyran-4-ylhydrazine1,1-Dimethylethyl 2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate was added to 1,4-Dioxane (10 mL) followed by hydrochloric acid (4M in 1,4-Dioxane, 10 mL, 329 mmol). The reaction mixture was stirred at room temperature for 60 h. The reaction mixture was filtered to afford the product as a solid, 1.02 g. (72%). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.45 (qd, J=l 1.79, 4.29 Hz, 2 H), 1.81 – 2.01 (m, 2 H), 3.00 – 3.19 (m, 1 H), 3.20 – 3.35 (m, 2 H), 3.78 – 3.97 (m, 2 H), 6.5-9.5(br m, 3 H).

693287-79-5 tert-Butyl 2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate 45092245, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; GLAX0SMITHKLINE LLC; BURGESS, Joelle, Lorraine; JOHNSON, Neil, W.; KNIGHT, Steven, David; LAFRANCE, Louis, Vincent, III; MILLER, William, H.; NEWLANDER, Kenneth, Allen; ROMERIL, Stuart, Paul; ROUSE, Meagan, B.; SUAREZ, Dominic; TIAN, Xinrong; VERMA, Sharad, Kumar; WO2013/39988; (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.33821-94-2,2-(3-Bromopropoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

A mixture of D147 (1 .00 g, 5.02 mmol), 2-(3-bromopropoxy)tetrahydro-2H-pyran (1 .12 g, 5.02 mmol) and K2CO3(1 .39 g, 10.04 mmol) in DMF (20 mL) was heated at 80 C for 3 hrs. The reaction mixture was poured into ice water (60 mL), and extracted with EtOAc (2×30 mL). The organic layer was washed with brine (3×40 mL), dried, filtered and concentrated. The crude was purified by column chromatography on silica gel (PE: EtOAc= 1 : 1 ) to give the title compound as a yellow solid (1 .526 g, yield 89%).

33821-94-2 2-(3-Bromopropoxy)tetrahydro-2H-pyran 2777988, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DING, Xiao; HO, Ming-Hsun; REN, Feng; YU, Haihua; ZHAN, Yang; (290 pag.)WO2019/12093; (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.110238-91-0,Methyl tetrahydro-2H-pyran-4-carboxylate,as a common compound, the synthetic route is as follows.

Step 1: Synthesis of (Tetrahydro-pyran-4-yl)-methanol To a solution of 250 mL of LiAlH4 (2.3M solution in THF, 0.575 mol) in THF (200 mL) is added dropwise a solution of 130 mL (0.974 mol) of tetrahydro-pyran-4-carboxylic acid methyl ester in THF (900 mL) under nitrogen atmosphere (CAUTION: highly exothermic[reaction]). The temperature is kept at 40-45 C. with an ice-bath. Upon complete addition, the reaction is stirred at room temperature for 1.5 h. The reaction is cooled in an ice-bath and quenched with addition of water (22 mL), 15% aqueous NaOH solution (21 mL) and water (66 mL). The resulting precipitate is removed by filtration through Celite and is rinsed with THF (300 mL). The filtrate is concentrated under reduced pressure to afford 102.5 g of (tetrahydro-pyran-4-yl)-methanol as a clear oil. Yield: 91%; 1H-NMR (400 MHz, CHLOROFORM-d) delta ppm 1.20-1.39 (2H, m), 1.56-1.83 (3H, m), 2.03 (1H, br. s.), 3.29-3.52 (4H, m), 3.89-4.05 (2H, m),

110238-91-0 Methyl tetrahydro-2H-pyran-4-carboxylate 2773520, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Boehringer Ingelheim International GmbH; US2010/76029; (2010); 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 A: Preparation of 4-methylenetetrahydro-2H-pyran: A solution of dihydro-2H-pyran-4(3H)-one (2.50g; 25.0mmol) in THF (50mL) was sparged with nitrogen for 15 minutes. The solution was cooled to 5 C under nitrogen with stirring. A solution of Tebbe reagent (bis(cyclopentadienyl)-mu-chloro(dimethylaluminum)-mu-methylenetitanium) (25.0 mmol; 0.50 M solution in toluene; Sigma- Aldrich Chemical Co.) was added. The mixture was allowed to warm to ambient temperature. Ether was added (400 mL). The reagent was quenched by the careful addition of 0.1M sodium hydroxide (10 mL). (The quench is highly exothermic with considerable effervescence). The resulting solution was dried (sodium sulfate) and filtered through a mixture of Celite and alumina washing the filter cake with ether. The filtrate was partially concentrated to remove the majority of the ether at 50 C and a pressure of 580 mm Hg. The resulting mixture was diluted with pentane, filtered through Celite and then partially concentrated as previously (taking care not to lose the volatile product). The resulting solution in toluene/pentane was continued to the next step without characterization of the product.

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

Reference£º
Patent; ARRAY BIOPHARMA INC.; BOYS, Mark Laurence; BURGESS, Laurence, E.; GRONEBERG, Robert, D.; HARVEY, Darren, M.; HUANG, Lily; KERCHER, Timothy; KRASER, Christopher, F.; LAIRD, Ellen; TARLTON, Eugene; ZHAO, Qian; WO2011/130146; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics