Heterocyclic Building Blocks-Tetrahydropyran

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.

2-(4-Oxanyl)ethanol To a stirring suspension of lithium aluminum hydride (5.10 g, 138 mmol) in THF (200 mL) at 0 C. was added drop-wise a solution of ethyl 2-(4-oxanyl)acetate (22.0 g, 138 mmol) in THF (50 mL). The reaction mixture was then heated at reflux overnight. After cooling the mixture in an ice bath, ether (300 mL) was added, followed by drop-wise addition of 5N NaOH, until the formation of heavy white precipitate is complete. The suspension was filtered and the filtrate dried (K2CO3), filtered and concentrated by rotary evaporation to give a colorless liquid (17.7 g, 100%).

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

Reference£º
Patent; Targacept, Inc.; US2004/220214; (2004); 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 1: Tetrahydro-2H-pyran-4-yl methanesulfonate To a solution of tetrahydro-2H-pyran-4-ol (20 g) in tetrahydrofuran (150 mL) and triethylamine (28.5 mL) is slowly added methanesulfonyl chloride (15.5 mL), while keeping the temperature below 30 C. The mixture is stirred for 12 hours at room temperature. The precipitate is filtered off and washed twice with tetrahydrofuran. The combined organic phases are concentrated and partitioned between ethyl acetate and water. The organic phase is dried (Na2SO4) and concentrated to give the title compound. Yield: 29.4 g; TLC: rf=0.36 (silicagel, petrole ether/ethyl acetate 1:1); Mass spectrum (ESI+): m/z=198 [M+NH4]+.

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; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; US2013/252937; (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.951127-25-6,tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

At room temperature, 2b (0.2 g, 0.92 mmol) was dissolved in dimethylacetamide (4 mL)Intermediate 1 (0.275 g, 0.84 mmol) and benzenesulfonic acid (0.187 g, 1.01 mmol) were added and stirred at room temperature for 2 hours.Sodium tris (acetoxy) borohydride (0.231 g, 1.09 mmol) was added to the reaction solution, and the reaction was continued at room temperature for 16 hours.After cooling to 0 C, water (15 mL) and ammonia (1 mL) were added successively to precipitate a white solid.The reaction solution was filtered and the filter cake was washed with water (5 mL x 2), dried, and the filter cake was dried to give the white solid 2c (0.22 g, yield 49.5%).

951127-25-6 tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate 44193925, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Sichuan Haisco Pharmaceutical Co.,Ltd; FAN, JIANG; CHEN, QINGPING; JIANG, WEI; ZHENG, SUXIN; YE, FEI; (128 pag.)TW2017/8221; (2017); A;,
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

Magnesium (1.68 g, 69.1 mmol) was stirred under argon for 40h, 50mL THF was added. Than dropwise addition of 4-(2-bromoethyl)oxane (10 ml, 69 mmol) in 15mL THF. The reaction mixture was heated up to 550, gas evolution was ob served. The reaction mixture was stirred for 1 h at 50, than cooled down to rt. The solutio n was used in the following reaction without any workup

4677-20-7 4-(2-Bromoethyl)tetrahydropyran 22637012, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; THE BROAD INSTITUTE, INC.; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; FURST, Laura; SERRANO-WU, Michael, H.; LEMKE, Chris; MCKINNEY, David; FITZGERALD, Mark; NASVESCHUK, Christopher; LAZARSKI, Kiel; FERRARA, Steven, James; WEI, Guo; MCCARREN, Patrick, Ryan; THEDE, Kai; MENGEL, Anne; CHRIST, Clara; KUHNKE, Joachim; JOHANNES, Sarah, Anna, Liesa; BUCHGRABER, Philipp; KLAR, Ulrich; SACK, Ulrike; KAULFUSS, Stefan; FERNANDEZ-MONTALVAN, Amaury, Ernesto; WERBECK, Nicolas; MOeNNING, Ursula; NOWAK-REPPEL, Katrin; (475 pag.)WO2019/96911; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1228779-96-1, 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound 4-3 was dissolved in dichloromethane,Add (3 eq) EDCI, (0.3 eq) DMAP,After stirring at room temperature for half an hour, compound 1-5 (0.8 eq) was added.It is then reacted at room temperature for 6-8 hours. After the reaction is completed, the reaction is quenched with water.Extract three times with dichloromethane, and combine the organic phases with saturated brine.After drying anhydrous sodium sulfate, mix the sample on the column.CH2Cl2: MeOH = 100:1 to 40:1 gave compound S4.

The synthetic route of 1228779-96-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhang Ao; Tan Wenfu; Liu Xiaohua; Huang Wenjing; Zhang Yu; Yang Jun; (37 pag.)CN110143974; (2019); A;,
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

(f) 2-[2-(tetrahydropyran-4-yl)-ethylamino]-adenosine-5′-N-ethylcarboxamide; the starting 2-(tetrahydro-pyran-4-yl)-ethylamine can be prepared from tetrahydropyran-4-one e.g. by Wittig condensation with diethyl cyanomethyl phosphonate followed by hydrogenation and reduction with lithium aluminum hydride.

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

Reference£º
Patent; King Pharmaceuticals Research and Development, Inc.; US6368573; (2002); B1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

25850-22-0, 2,2-Dimethyltetrahydro-2H-pyran-4-amine is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5-Benzyloxymethyl isoxazole-3-carboxylic acid (0.24 g, 1.0 mmol), 4-amino-2,2-dimethyltetrahydropyran (0.18 ml, 1.2 mmol) And 1-hydroxybenzotriazole (0.01 g, 0.1 mmol) Was added to chloroform (amylene added product) (2.5 mL). To the mixture, 1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (0.24 g, 1.2 mmol) was added at room temperature, After stirring overnight, Dilute hydrochloric acid was added, It was extracted twice with chloroform. The organic layer was passed through a short column of silica gel to remove impurities, And concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, Represented by the following equation N- (2,2-dimethyltetrahydropyran-4-yl) -5-benzyloxymethyl isoxazole-3-carboxamide (Hereinafter referred to as the present amide compound (335)) 0.29 g was obtained.

The synthetic route of 25850-22-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; SUMITA, YUSUKE; (264 pag.)JP2015/51963; (2015); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

101691-94-5, 4-(Iodomethyl)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of tert-butyl 5-(6-cyclopropyl-2-oxo-l,2-dihydropyridine-4-carbonyl)-3,4,5,6- tetrahydropyrrolo[3,4-c]pyrrole-2(lH)-carboxylate (385 mg, 985 muiotaetaomicron), potassium carbonate (272 mg, 1.97 mmol) and 4-(iodomethyl)tetrahydro-2H-pyran (459 mg, 1.97 mmol) in acetonitrile (8 mL) was heated at 90C for 48 h, then partitioned between sat. aq. ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was chromatographed (silica gel; gradient dichloromethane to dichloromethane/methanol/25% aq. ammonia solution 95:5:0.25) to produce the title compound (390 mg, 84%). White foam, MS: 470.3 (M+H)+.

The synthetic route of 101691-94-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; MATTEI, Patrizio; HERT, Jerome; HUNZIKER, Daniel; RUDOLPH, Markus; SCHMITZ, Petra; DI GIORGIO, Patrick; (87 pag.)WO2017/50792; (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.5631-96-9,2-(2-Chloroethoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

EXAMPLE 12 3,3-Dimethyl-5-fluoro-1-(2-hydroxyethyl)-1,3-dihydro-2H-indol-2-one: 5-Fluoro-1,3-dihydro-2H-indol-2-one (2.4 g, 15.9 mmol) (prepared according to the method of Clark et al., Synthesis (1991) 871) was dissolved in freshly distilled tetrahydrofuran with tetramethylethylenediamine (3.7 g, 31.9 mmol) and was cooled to -75 C. under nitrogen. nButyllithium (2.4 equivalents) was added and the mixture was stirred at -75 C. for 40 minutes. Iodomethane (9 g, 63 mmol) was added and the mixture was allowed to warm to room temperature. After two hours’ stirring at this temperature, water (5 ml) was added and the mixture was concentrated under reduced pressure, the resulting oil was taken up in dichloromethane, washed with dilute hydrochloric acid, dried (MgSO4), filtered and concentrated to dry under reduced pressure to give a yellow oil. This oil was dissolved in N-methylpyrrolidone and stirred at room temperature under nitrogen. Sodium hydride (0.625 g, 15.6 mmol) was added and the mixture was stirred until gas evolution ceased. 2-(2-Chloroethoxy)tetrahydro-2H-pyran (2.5 g, 15 mmol) and sodium iodide (0.1 g, 0.66 mmol) was added and the mixture was warmed to 75 C. for 15 hours. Water was added and the mixture was concentrated under reduced pressure. The residue was taken up in ethyl acetate, washed (*3) with water, dried (MgSO4), filtered and concentrated under reduced pressure. The resulting oil was taken up in methanol, para toluenesulphonic acid (0.1 g, 0.5 mmol) was added and the mixture was stirred at room temperature for 12 hours. The mixture was concentrated under reduced pressure, taken up in ethyl acetate, washed (*3) with aqueous sodium hydrogen carbonate solution dried (MgSO4), filtered and concentrated under reduced pressure. The resulting oil was purified by column chromatography on silica gel, (eluent hexane/ethyl acetate) to give 3,3-dimethyl-5-fluoro-1-(2-hydroxyethyl)-1,3-dihydro-2H-indol-2-one as a yellow oil. MS shows 224 (MH+) base peak and 241 (M+NH4)

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

Reference£º
Patent; Eli Lilly and Company Limited; US5773448; (1998); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

388109-26-0, Ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 To a solution of ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate (1.0 g, 5.81 mmol) in DCM (30 mL) was added DIPEA (1.22 mL, 6.97 mmol) and Tf2O (1.08 mL, 6.39 mmol) at -78 C., then it was warmed up to room temperature and stirred at room temperature for 2 h, the solution was diluted with DCM, washed with Sat. NaHCO3, brine, dried and concentrated to give ethyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydro-2H-pyran-4-carboxylate as crude product (2 g).

As the paragraph descriping shows that 388109-26-0 is playing an increasingly important role.

Reference£º
Patent; Global Blood Therapeutics, Inc.; Metcalf, Brian W.; US2015/209443; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics