Category: 23462-75-1

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

23462-75-1, Dihydro-2H-pyran-3(4H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of tetrahydropyran-3-one (0.25g) and 2-amino-2-(4-bromophenyl)acetamide (D1 ) (0.572g) and H-Y Zeolites (0.57g) in methanol (25ml) was refluxed under argon overnight. The mixture was filtered through Kieselguhr and the solvent was removed to give crude title compound as a yellow solid which was used without purification (712mg). Mass spectrum Found 311/3 (MH+)., 23462-75-1

The synthetic route of 23462-75-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2009/34061; (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.23462-75-1,Dihydro-2H-pyran-3(4H)-one,as a common compound, the synthetic route is as follows.,23462-75-1

A solution of tert-butyl hydrazinecarboxylate (6.6 g, 50 mmol) and dihydro-2H-pyran-3(4H)-one (5 g, 50 mmol) in MeOH (50 mL) was stirred at 15 C. for 2 hours. The mixture was concentrated to remove MeOH and the crude was purified by column chromatography on silica gel (petroleum ether:ethyl acetate=1:1) to afford tert-butyl 2-(dihydro-2H-pyran-3(4H)-ylidene)hydrazine-1-carboxylate (10 g, 47 mmol, 93% yield).

23462-75-1 Dihydro-2H-pyran-3(4H)-one 90109, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; H. Lundbeck A/S; Juhl, Karsten; Jessing, Mikkel; Langgard, Morten; Vital, Paulo Jorge Vieira; Marigo, Mauro; Kehler, Jan; Rasmussen, Lars Kyhn; (27 pag.)US2017/291901; (2017); 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.

Dihydro-2//-pyran-3(4H)-one (100 mg, 1.00 mmol), /er/-butyl carbazate (145 mg, 1.10 mmol, Ll equiv) and acetic acid (0.280 niL, 4.99 mmol, 5 equiv) were combined in 1 ,2-dichloroethane(3 raL), stirred at ambient temperature for 10 minutes and treated with sodium triacetoxyborohydride (296 mg, 1,34 mmol, 1.4 equiv). After stirring for 1 hour, the mixture was poured into water and extracted with ethyl acetate (3 x 50 niL), The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo to provide the titled compound., 23462-75-1

23462-75-1 Dihydro-2H-pyran-3(4H)-one 90109, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK SHARP &; DOHME CORP.; BESHORE, Douglas, C.; KUDUK, Scott, D.; WO2010/123716; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

23462-75-1, Dihydro-2H-pyran-3(4H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 Methylmaganesium bromide (1.831 mL, 5.49 mmol) was added dropwise via syringe to a solution of dihydro-2H-pyran-3(4H)-one (500 mg, 4.99 mmol) in Diethyl ether (50 mL) at -20 C. and stirred at this temp for 1 hr before warming up to RT. The reaction was quenched with sat. ammonium chloride and extracted with ether. The organic layer was washed with brine, collected, dried over MgSO4, filtered and partially evaporated to give the crude product 3-methyltetrahydro-2H-pyran-3-ol (480 mg, 83% yield) as an oil. 1H NMR (400 MHz, CHLOROFORM-d) delta 3.90-3.81 (m, 1H), 3.55-3.50 (m, 1H), 3.40 (td, J=11.3, 2.8 Hz, 1H), 3.31 (d, J=11.3 Hz, 1H), 2.16 (br. s., 1H), 1.94-1.81 (m, 1H), 1.78-1.69 (m, 1H), 1.59-1.47 (m, 2H), 1.18-1.11 (m, 3H)., 23462-75-1

23462-75-1 Dihydro-2H-pyran-3(4H)-one 90109, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P. V. K. Suresh; Scola, Paul Michael; US2013/115190; (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.23462-75-1,Dihydro-2H-pyran-3(4H)-one,as a common compound, the synthetic route is as follows.

To a stirred solution of the dihydro-2H-pyran-3(4H)-one (commercially available from Pharm lab Product list, 21.6 g, 0.216 mol) in 160 ml of dry THF , trimethyl silyl chloride(58.7g, 68.5 ml, 0.54 mol) was added under argon at room temperature, then the mixture was allowed to stir 10 minutes .At this mixture triethylamine (59.7g, 82.2 ml, 0.59 mol) was added dropwise and under vigorous stirring (strong precipitation). The resulting suspension was heated to reflux for 48 hours, then the mix was cooled to r.t and concentrated to 1/3 of the volume at the rotavapor (T=40C, p=200 mbar). At this crude 300 ml of pentane were added to allow the complete precipitation of TEA.HCI and the suspension was filtered.The solid was washed with 100 ml of pentane and the resulting filtrate was separated.The desired product was isolated by fract. Distillation; pentane and THF residue were removed at athmospheric pressure and the sililenolether was isolated at Tdist=58-60C p=5mbar. Obtained 28.7 g of the title compound as colourless oilMS (ES) (mlz): 172 [M+H]+1H NMR (CDCI3 ) :delta 0.20 (s,9H), 1.92-2.32 (m, 2H), 3.67 (t, J=5.5 Hz, 2H), 3.78-3.95 (m,2H), 4.78-5.05 (m,1 H), 23462-75-1

23462-75-1 Dihydro-2H-pyran-3(4H)-one 90109, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Glaxo Group Limited; WO2009/43883; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

23462-75-1, Dihydro-2H-pyran-3(4H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 23: 3-methyl-8-(tetrahydro-2H-pyran-3-vn-4-((4-r3-(trifluoromethyl)phenvnpiperazin-1-yl)carbonyl)-1-oxa-8-azaspiror4.51dec-3-en-2-one Triethylamine (0.08 mL, 0.65 mmol) and dihydro-pyran-3-one (108 mg 1.08 mmol) were added into a solution of 3-methyl-4-({4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}carbonyl)-1-oxa-8- azaspiro[4.5]dec-3-en-2-one dihydrochloride (Example 1 , 100 mg, 0.20 mmol) in anhydrous dichloroethane (5 mL) cooled at 0C. Sodium triacetoxyborohydride (137 mg, 0.65 mmol) and trimethylorthoformate (120 mg, 1.08 mmol) were added and the resulting mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted with dichloromethane (20 mL) and washed with water (20 mL) and brine (20 mL). The organic layer was dried (MgS04) and concentrated under vacuum. After purification by flash chromatography (silica), the title compound was obtained as a white solid. 1H NMR (CDCI3, 400 MHz): delta 7.45-7.42 (m, 1 H), 7.24 (d, J = 9.0 Hz, 1 H), 7.20 (s, 1 H), 7.11 (d, J = 7.6 Hz, 1 H), 3.81-3.80 (m, 2H), 3.71-3.69 (m, 2H), 3.55 (s, 2H), 3.15 (s, 4H), 2.81-2.80 (m, 2H), 2.32-2.31 (m, 4H), 2.17 (s, 2H), 1.89-1.88 (m, 2H), 1 .75 (s, 3H), 1.69-1.61 (m, 2H), 1.48-1.38 (m, 3H). LCMS (Method D): Mass found (M+ 508.3), Rt (min): 3.88, Area (%): 93.6 (Max. Chrom.), 94.5 (254 nm). HPLC (Method A): Rt (min): 3.89, Area (%): 93.6 (Max. Chrom.), 94.4 (254 nm).

23462-75-1, The synthetic route of 23462-75-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ARES TRADING S.A.; JORAND-LEBRUN, Catherine; SWINNEN, Dominique; GERBER, Patrick; KULKARNI, Santosh; WO2012/130915; (2012); 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.

To a suspension of 3-((1R,5S,9r)-9-methoxy-3-azabicyclo[3.3.1]nonan-9-yl)benzamide hydrochloride (300 mg, 0.97 mmol), dihydro-2H-pyran-3(4)-one (194 mg, 1.93 mmol) in tetrahydrofuran (16 ml) was added triethylamine (0.34 ml, 2.50 mmol) and the reaction mixture was stirred at room temperature for 20 minutes. Sodium triacetoxyborohydride (614 mg, 2.89 mmol) was added and the mixture stirred at room temperature overnight. The reaction was quenched with aqueous solution of sodium hydrogen carbonate and extracted with dichloromethane (*3). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by silica chromatography eluting with 1-5% methanol in dichloromethane. The enantiomers were separated by chiral supercritical fluid chromatography to give 3-((1R,5S,9s)-9-methoxy-3-((S)-tetrahydro-2H-pyran-3-yl)-3-azabicyclo[3.3.1]nonan-9-yl)benzamide (81 mg, 25% yield) and 3-((1R,5S,9R)-9-methoxy-3-((R)-tetrahydro-2H-pyran-3-yl)-3-azabicyclo[3.3.1]nonan-9-yl)benzamide (71 mg, 19% yield). The stereochemistry was arbitrarily assigned.

23462-75-1, The synthetic route of 23462-75-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Alkermes, Inc.; Wynn, Thomas Andrew; Alvarez, Juan C.; Moustakas, Demetri Theodore; Haeberlein, Markus; Pennington, Lewis D.; US2019/241524; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

23462-75-1, Dihydro-2H-pyran-3(4H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a round-bottom flask equipped with a stir bar and placed under N2 atmosphere was added THF (50 mL), then trimethyl(trifluoromethyl)silane (1.03 mL, 6.99 mmol). The solution was cooled to 0 C and to the solution was added dihydro- 2H-pyran-3(4H)-one (500 mg, 4.99 mmol). The solution was stirred for 5 minutes at 0 C and then was allowed to warm to room temperature with stirring for 30 minutes. The solution was cooled to 0 C and to the solution was added aq 1M HC1 (50 mL). The mixture was stirred at room temperature overnight. The mixture was diluted with water and EtOAc and was transferred to a separatory funnel. The organic phase was isolated; washed with brine; dried over MgSC^, filtered; then concentrated in vacuo to afford 3-(trifluoromethyl)tetrahydro-2H-pyran-3-ol as a colorless oil (0.40 g, 47%). 1H-NMR (400MHz, CDC13) 5 4.01 – 3.93 (m, IH), 3.82 (dd, J=l 1.8, 2.5 Hz, IH), 3.60 (d, J=12.0 Hz, IH), 3.41 (td, J=l 1.8, 2.5 Hz, IH), 2.10 – 2.08 (m, 2H), 1.97 – 1.90 (m, IH), 1.82 (dd, J=12.9, 4.4 Hz, IH), 1.65 – 1.55 (m, IH)., 23462-75-1

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; GILLIS, Eric P.; BOWSHER, Michael S.; SCOLA, Paul Michael; WO2014/71007; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

23462-75-1, Dihydro-2H-pyran-3(4H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

23462-75-1, Dihydro-2H-pyran-3(4H)-one (4.00 g, 40.0 mmol) was dissolved in THF (32.0 mL) and chlorotrimethylsilane (12.8 mL, 100 mmol) was added. The reaction was stirred at room temperature for 10 minutes. Triethylamine (15.0 mL, 108 mmol) was then added dropwise under nitrogen. A white precipitate formed and the resulting suspension was heated to 70C over the weekend. The reaction mixture was cooled to room temperature and concentrated in vacuo. Pentane (80 mL) was added, the suspension was filtered, and the solid was washed with pentane (40 mL). The filtrate was concentrated in vacuo to give the title compound as a liquid that was used as is in the next step without further purification. 1H NMR (500 MHz, CDCI3) delta 4.98-4.92 (m, 1H), 3.88 (m, 2H), 3.69 (t, / = 5.5 Hz, 2H), 2.16 (m, 2H), 0.19 (s, 9H).

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

Reference£º
Patent; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew Lloyd; FULLER, Peter; GUERIN, David; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; MARTINEZ, Michelle; FALCONE, Danielle; TORRES, Luis; DENG, Yongqi; KURUKLASURIYA, Ravi; ZENG, Hongbo; BAI, Yunfeng; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146491; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics