Category: 29943-42-8

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

A) tert-butyl 2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate [0431] A solution of tetrahydro-4H-pyran-4-one (2.50 g) and tert-butyl hydrazinecarboxylate (3.47 g) in methanol (10 mL) was stirred at room temperature for 1 hr, and concentrated under reduced pressure. The residue was dissolved in THF (25 mL), acetic acid (4.3 mL) and sodium borohydride (0.525 g) were added thereto, and the mixture was stirred at 0C for 1 hr. To the reaction mixture was added 8N aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.34 g). 1H NMR (300 MHz, CDCl3) delta 1.35-1.54 (11H, m), 1.77 (2H, dd, J = 12.1 Hz, 2.3 Hz), 2.98-3.15 (1H, m), 3.40 (2H, td, J = 11.3 Hz, 2.3 Hz), 3.96 (3H, dt, J = 11.5 Hz, 3.7 Hz), 6.03 (1H, brs).

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

Reference£º
Patent; Takeda Pharmaceutical Company Limited; NARA, Hiroshi; DAINI, Masaki; KAIEDA, Akira; KAMEI, Taku; IMAEDA, Toshihiro; KIKUCHI, Fumiaki; EP2857400; (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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

Example 4 N-(4-Ethoxy-6-{4-oxo-2-[(tetrahydro-pyran-4-ylmethyl-amino)-4H-thiazol-5-ylidenemethyl}-quinolin-2-yl]-acetamide a) Preparation of c-(tetrahydro-pyran-4-yl)-methylammonium acetate A cold (ice water bath) solution of tetrahydro-4H-pyran-4-one (7.5 g, 75 mmol) and tosylmethylisocyanide (16.05 g, 82.4 mmol) in DME (125 ml) was treated with a suspension of potassium t-butoxide (16.8 g, 150 mmoles) in t-butyl alcohol (250 ml). The reaction mixture was stirred at room temperature for 31/2 hours, and then diluted with ether (250 ml). The mixture was successively washed with water and brine, then dried over sodium sulfate, filtered, and concentrated. The crude product was purified by short path distillation under high vacuum to give the nitrile as colorless oil (2.98 g). This material was dissolved in 1M borane/tetrahydrofuran (THF) (134 ml, 134 mmol) and stirred at rt overnight. Excess borane was quenched by adding methanol (rt, 1 h), and the mixture was concentrated to dryness. The residue was dissolved in 4N HCl/dioxane, stirred at rt for 1 h and then concentrated under reduced pressure. The solid residue was triturated with ether and collected by suction filtration. A suspension of this material (1.81 g, 11.9 mmol) in THF (30 ml) was treated with 1N NaOH (11.9 ml, 11.9 mmol) at rt for ? h. The THF was removed by distillation and the aqueous solution was saturated with NaCl then extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was treated with acetic acid (0.68 ml, 11.9 mmol) to provide, after drying in a vacuum oven, c-(tetrahydro-pyran-4-yl)-methylammonium acetate (1.71 g).

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

Reference£º
Patent; Chen, Li; Chen, Shaoqing; Michoud, Christophe; US2006/63804; (2006); 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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

Reference Example 1 : Tetrahvdro-pyran-4-carbonitriIe. To a solution of tetrahydro-pyran-4-one (2.0 g, 20.0 mmol) and tosyl methyl isocyanide (5.06 g, 25.9 mmol) in dimethoxyethane (15 mL) was added ethanol (1.5 niL). The reaction mixture was cooled to 0C and potassium tert-butoxide (5.57 g, 49.7 mmol) was added. The resulting reaction mixture was warmed to r.t. and stirred for Ih, then heated to 4O0C for 30 minutes. The mixture was cooled to r.t. and filtered. The resulting solid was washed with dimethoxyethane (3 x 15 mL), and the combined filtrates were evaporated to give a crude compound which was purified by column chromotography over 60-120 silica gel using 10-12% ethyl acetate in hexane to afford 5 tetrahydro-pyran-4-carbonitrile (1.05 g, 47 %) as a light yellow liquid., 29943-42-8

The synthetic route of 29943-42-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F2G LTD; WO2008/62182; (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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

To 75 g (0.75 mol) of tetrahydropyran-4-one in THF (150 mL) is added a suspension of 28.4 g (0.75 mol) LiAIH4 in THF (600 mL) under nitrogen atmosphere maintaining the temperature below 30 C with the aid of an ice-bath. Then the reaction is allowed to warm to RT and stirred for 5 h. The reaction is quenched by addition of sat. aq. NH4CI solution until effervescence ceased. The resulting precipitate is removed by filtration through Celite and washed with THF (150 mL). The filtrate is concentrated under reduced pressure to afford 71.1 g of tetrahydropyran-4-ol. Yield: 92%., 29943-42-8

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

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; BINDER, Florian; DOODS, Henri; MUELLER, Stephan, Georg; NICHOLSON, Janet, Rachel; SAUER, Achim; WO2014/184327; (2014); 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

Into a 250-mL 3-necked round bottom flask, was placed a solution of tetrahydropyran-4-one (5 g, 50.00 mmol, 1.00 equiv) in tetrahydrofuran (25 mL). This was followed by dropwise addition of a solution of LiAlH4 (3.8 g, 102.70 mmol, 2.00 equiv) in tetrahydrofuran (25 mL) with stirring at 0-5 C. The resulting solution was stirred for 3 h at 0-5 C. in a water/ice bath. The reaction was then quenched by the addition of 3.8 mL of water, 3.8 mL of 15% NaOH, and 11.4 mL of water. The mixture was dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum to yield 5 g (96%) of product as a yellow oil., 29943-42-8

The synthetic route of 29943-42-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Ardelyx, Inc.; Lewis, Jason G.; Jacobs, Jeffrey W.; Reich, Nicholas; Leadbetter, Michael R.; Bell, Noah; Chang, Han-Ting; Chen, Tao; Navre, Marc; Charmot, Dominique; Carreras, Christopher; Labonte, Eric; (323 pag.)US9301951; (2016); B2;,
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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

A solution of tetrahydro-4H-pyran-4-one (25 g, 250 mmol) and toluenesulfonylmethyl cyanide (53.7 g, 275 mmol) dissolved in ethylene glycol dimethylether (1 L) was cooled to 0 C. Added dropwise over 30 min was a solution of potassium t-butoxide (56 g, 500 mmol) dissolved in t-butanol (350 mL) and ethylene glycol dimethylether (150 mL). After stirring the resulting mixture for 3 h at room temp, diethyl ether (1 L) was added and the organic phase was washed with saturated aqueous NaHCO3. The organic phase was dried (Na2SO4) and concentrated. The residue was distilled at 39 C. 1.7 mm Hg to give the title compound as colorless oil (10.87 g, 39% yield). 1H NMR (300 MHz, CDCl3) delta: 3.91-3.83 (2H, m), 3.61-3.54 (2H, m), 2.89-2.80 (1H, m), 1.97-1.78 (4H, m).

29943-42-8, The synthetic route of 29943-42-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Bristol-Myers Squibb Company; US2008/306051; (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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

To a solution of tetrahydro-pyran-4-one (1.3 kg, 12.98 mol) and carbonic acid dimethyl ester (1 1 .69 kg, 129.8 mol) was added solid potassium te/t-butoxide (1 .89 kg, 16.08 mol) in portions at -10C over 2 h under nitrogen protection. The suspension was stirred at room temperature 10 h after the addition. LCMS (215nm) indicated that tetrahydro-pyran- 4-one had been completely consumed. The reaction was acidified by HCI (2 N) to pH 6~7 and then the phases were separated. The organic phase was washed with water (3 Lx2) and the combined aqueous phases were extracted with MTBE (2.5 Lx2). The combined organic phase was concentrated under reduced pressure at 25C to remove most of MTBE. The residue was distilled out by oil pump (-200 Pa) at 74 C to give the title compound as colorless oil (545 g, 26.3%). CHN analysis: calculated (results). C 53.16 (53.10), H 6.37 (6.245), N 0.00 (0.00)., 29943-42-8

As the paragraph descriping shows that 29943-42-8 is playing an increasingly important role.

Reference£º
Patent; NOVARTIS AG; CHEN, Christine Hiu-Tung; CHIN, Noel Chin; DIPIETRO, Lucian V.; FAN, Jianme; PALERMO, Mark G; SHULTZ, Michael David; TOURE, Bakary-Barry; WO2013/8217; (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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

Intermediate 4Tetrahydro~2H-pyran-4-carbonitrile. A solution of tetrahydro-4Hr-pyran-4- one (25 g, 250 mmol) and toluenesulfonylmethyl cyanide (53.7 g, 275 mmol) dissolved in ethylene glycol dimethylether (1 L) was cooled to 0 C. Added dropwise over 30 min was a solution of potassium t-butoxide (56 g, 500 mmol) dissolved in t-butanol (350 mL) and ethylene glycol dimethylether (150 mL). After stirring the resulting mixture for 3 h at room temp, diethyl ether (1 L) was added and the organic phase was washed with saturated aqueous NaHCO3. The organic phase was dried (Na2SO4) and concentrated. The residue was distilled at 39 C 1.7 mm Hg to give the title compound as a colorless oil (10.87 g, 39% yield). 1H NMR (300 MHz, CDCl3) delta: 3.91-3.83 (2H, m), 3.61-3.54 (2H, m), 2.89-2.80 (IH, m), 1.97-1.78 (4H, m)., 29943-42-8

As the paragraph descriping shows that 29943-42-8 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/58646; (2007); 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

(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, The synthetic route of 29943-42-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Ciba-Geigy Corporation; US4968697; (1990); A;,
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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

N-Methyl-N-(tetrahydro-2H-pyran-4-yl)amine At -70 C., 170 g (5.5 mol) of gaseous methylamine were introduced into 1.5 l of methanol. The solution was admixed dropwise with 100 g (1 mol) of sulfuric acid. 100 g (1 mol) of tetrahydro-4H-pyran-4-one and 36.4 g (0.6 mol) of sodium borocyanohydride were added in succession, and the mixture was stirred at room temperature for 3 days, resulting in a white precipitate. The solution was filtered and the filtrate was distilled. B.p. 56-58 C. (12 mm), yield 96 g. 1H NMR (270 MHz, in CDCl3): delta=1.30 (s, 1H), 1.38 (dq, 2H), 1.85 (dd, 2H), 2.43 (s, 3H), 2.57 (tt, 1H), 3.41 (dt, 2H), 3.99 (dt, 2H)., 29943-42-8

As the paragraph descriping shows that 29943-42-8 is playing an increasingly important role.

Reference£º
Patent; BASF Aktiengesellschaft; US6277790; (2001); B1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics