Day: October 28, 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.185815-59-2,4-Isobutyldihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

185815-59-2, Example 4: Preparation of C3R)-5-methyl-3-(‘2-oxo-2(r(lRVl-phenylethvnamino>ethv? hexanoic acid compound (24); [0078] A three-necked flask equipped with an addition funnel, thermometer pocket, drying tube and a mechanical stirrer), was charged with tert-butyl methyl ether (100 ml), (R)-(+)-phenylethylamine (43.05 g, 0.355 mole) and 4-dimethylaminopyridine (0.258 g, 0.0021 mole). The mixture was cooled to a temperature of 0-5C, followed by addition of a solution of 3-isobutyl glutaric anhydride (40 g, 0.235 mole) in tert-butyl methyl ether (100 ml), over a period of 15-20 minutes, and stirring for additional 1.5-2 hours, at a temperature of 0-5C. The mixture was then extracted with 5 percent aqueous solution of NaHCO3 solution (700 ml), and the aqueous phase was washed with tert-butyl methyl ether (1 x 100 ml). The pH of the aqueous phase was adjusted to 2-2.5 by adding a 1-12N solution of hydrochloric acid. The aqueous phase was further extracted with ethyl acetate (I x 200 ml), followed by drying the combined ethyl acetates extracts over anhydrous sodium sulfate, and stripping off the solvents, to obtain a residue. The residue was crystallized from ethyl acetate and toluene mixture to get 44.5 g (70 percent yield) of a white solid of (3R)-5- EPO memyl-3-(2-oxo-2-{[(lR)-l-phenylethyl]amiho}ethyl)hexanoic acid with an optical purity of 99.19 percent, as measured by chiral HPLC.

As the paragraph descriping shows that 185815-59-2 is playing an increasingly important role.

Reference£º
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2007/35789; (2007); 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

693287-79-5, To a solution of tetrahydropyran-4-one (71.6 g, 715 mmol) in methanol (2 L) was added tert-butylcarbazate (100 g, 758 mmol) at ambient temp. The mixture was stirred at ambient temp for 20 h. The reaction mixture was concentrated under reduced pressure to dryness to afford a white solid (154 g). To a suspension of the white solid (154 g, 715 mmol) in water (1 L) was added acetic acid (500 mL, 8.73 mol) and the mixture was stirred for 30 min to get a clear solution. To this solution, solid NaCNBH3 (44.5 g, 708 mmol) was added portion-wise. The mixture was stirred at ambient temp for 2 h. The mixture was then transferred to a 12 L flask, cooled to 0 C., and quenched with 1N NaOH (8.73 L, 8.73 mol). The mixture was extracted with CH2Cl2 (3¡Á3 L) and dried over Na2SO4. The organic layer was filtered and concentrated to afford a white solid (164 g, contains 15% of N-acetyl-N’-Boc-hydrazine derivative). Chromatography [silica, ethyl acetate/MeOH (95:5] gave 94 g of 90% pure boc-hydrazine. A solution of boc-hydrazine (50 g, 231 mmol) in methanol (500 mL) was added a solution of HCl in dioxane (462 mL, 1.85 mol, 4.0 M). The mixture was stirred at ambient temp overnight. Concentration of the reaction mixture under reduced pressure afforded the title compound as a white solid (43 g, 98%). 400 MHz 1H NMR (DMSO) delta 3.85-3.82 (m, 2H), 3.27-3.21 (m, 2H), 3.13-3.05 (m, 1H), 1.88-1.84 (m, 2H), 1.48-1.38 (m, 2H). MS: (M+H m/z=117.2).

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

Reference£º
Patent; Pfizer Inc; US2009/30003; (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.220641-87-2,N-Methyltetrahydro-2H-pyran-4-amine,as a common compound, the synthetic route is as follows.

To a solution of A2 (100 mg, 0.3 12 mmol) in DCM (4 mL) was added TEA (156 mg, 1.55 mmol) and HATU (112 mg, 0.468 mmol) at 25 C. After stirring at 25 C for 30 minutes, N-methyltetrahydro-2H- pyran-4-amine (57.4 mg, 0.499 mmol) was added. The mixture was stirred at 25 C for 16 hrs, quenchedwith water (4 mL) and extracted with DCM (2 x 4 mL). The organic layers were washed with brine (2 x5 mL), dried over Na2SO4 , filtered, concentrated in vacuo to give a crude product, which was purifiedby silica gel chromatography eluted with PE/EtOAc = 3/1 to afford the desired compound. Thecompound was lyophilized to give a solid (80 mg) that was further re-crystallized (85 C) from MeCN(2 mL) and water (20 mL) to give Compound 10 (66 mg, 51%) as a solid.1H NMR (400 MHz, CDCl3) delta 4.85-4.70 (m, 0.5H), 4.15-3.95 (m, 2H), 3.55-3.40 (m, 1.5H), 2.90-2.70 (m, 3H), 2.69-2.60 (m, 1H), 2.35-2.20 (m, 1H), 1.90-1.60 (m, 1OH), 1.59-1.16 (m, 18H),1.15-1.00 (m, 3H), 0.72 (s, 3H).LCMS Rt = 1.005 min in 2.0 mm chromatography, 30-90 AB, purity 100%, MS ESI calcd. for C26H44N03 [M+Hf?418, found 418.

220641-87-2, 220641-87-2 N-Methyltetrahydro-2H-pyran-4-amine 6991950, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; SAGE THERAPEUTICS, INC.; ROBICHAUD, Albert, J.; MARTINEZ BOTELLA, Gabriel; HARRISON, Boyd, L.; SALITURO, Francesco, G.; GRIFFIN, Andrew; BLANCO-PILLADO, Maria, Jesus; (296 pag.)WO2018/13613; (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.388109-26-0,Ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate,as a common compound, the synthetic route is as follows.

O1 161 Step 1: i?o a solution of eth I 3-oxotetrahvdro2i 1.p ran-4-?carhoxvlate (1 0 g, 5.8mmo )in 1X?M (30 mu was added D1PI.A 1 .22 ml., 6.97 mmcl) and FfO (1 08 ml., 6.39mmoi at 78 C. then it us warmed up to room temperature and stirred at roomtemepemature fhr 2 h, the o1ution as diluted with DCM, ashcd with Sat. aH(O, brine.dried and concentated to give eih3 I 5?1((trifluoronieth l)sulton I oxy).?3,6?dih dio-21 lp mam4-cai boxy late as crude product (2 ,

388109-26-0, 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.; WO2015/116061; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

223734-62-1, 2-((S)-Dec-1-yn-5-yloxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2: Preparation of chiral benzyl alkynol (3).; Table 2Triethylamine 101.19 0.68 g 0.0068Toluene NA 10 ml NAProcedure: A 50-mL, two-necked, round-bottomed flask equipped with a magnetic stirrer and stir bar was charged with zinc triflate (3.17 g, 0.0087 mol) and (+)-N-methylephedrine (1.22 g, 0.0068 mol) in toluene (5 mL). To this mixture triethylamine was added (0.68 g, 0.0068 mol) and this gelatinous mixture was stirred at ambient temperature for 1 -2 h. To this mixture was then added a solution of alkyne (1.57 g, 0.0065 mol) in toluene (4 mL), stirred at ambient temperature for 15-30 minutes followed by addition of a solution of aldehyde (2) (0.50 g, 0.0026 mol in 1-2 mL toluene). Progress of the reaction was monitored by TLC (Note 1). After stirring the mixture at room temperature for 16 h, TLC indicated completion of reaction. The reaction mixture was quenched by slow addition of water (10 mL). This was stirred for 5-10 minutes and organic layer containing desired compound was separated. The aqueous layer was extracted with ethyl acetate (10 mL). The combined organic layers were washed with brine (10 mL), dried over anhydrous sodium sulfate, filtered and the filtrate concentrated in vacuo to obtain a crude product. The crude product wa~ purified by column chromatography using 250-400 mesh silica gel. A solvent gradient of ethyl acetate in hexanes (5-20%) was used to elute the product from the column. All fractions containing the desired pure product were combined and concentrated in vacuo to give pure chiral benzyl alkynol (3, 700 mg, -70%). The structure was consistent with spectral data.1H NMR (CDC13, 300 MHz) delta 0.84 (t, 3H, J = 6 Hz), 1.25 – 1.82 (m, 17H), 2.28 (t, 1H, J = 6 Hz), 2.34 -2-42 (m, 2H), 3.42 -3.52 (m, 1H), 3.61 – 3.74 (m, 3H), 3.78 (s, 3H), 3.81 -3.95 (m, 1H), 4.61 (s, 2H), 4.68 (m, 1H), 4.94 – 5.01 (m, 2H), 5.62 (br s, 1H), 5.97 – 6.07 (m, 1H), 6.76 (d, 1H, J= 8 Hz), 7.16 -7.27 (m, 1H), 7.38 -7.43 (m, 1H); 13C NMR (CDC13, 75 MHz) 84.75, -4.38, -3.49, 14.12, 14.16, 14.84, 15.52, 18.06, 18.38, 20.04, 20.24, 22.70, 24.76, 25.25, 25.56, 25.72, 25.94, 29.67, 31.22, 31.28, 32.05, 32.11, 32.65, 33.41, 34.01 , 35.08, 52.22, 62.36, 62.84, 63.09, 66.04, 75.41, 76.44, 76.68, 80.83, 81.22, 85.57, 86.01, 97.31, 98.85, 110.89, 1 14.80, 119.77,1 19.82, 125.56, 127.11, 127.16, 136.46, 136.52, 142.66, 142.73, 155.83, 169.68; MS: (M+Na) 495.6.Note 1 : Completion of the reaction was monitored by thin layer chromatography (TLC) using a thin layer silica gel plate; eluent: 20% ethyl acetate in hexanes., 223734-62-1

As the paragraph descriping shows that 223734-62-1 is playing an increasingly important role.

Reference£º
Patent; UNITED THERAPEUTICS CORPORATION; BATRA, Hitesh; PENMASTA, Raju; SHARMA, Vijay; TULADHAR, Sudersan M.; WALSH, David A.; WO2011/153363; (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.25637-16-5,4-Bromotetrahydropyran,as a common compound, the synthetic route is as follows.

Compound 10-rac (100 mg, 0.28 mmol) and 37 4-bromotetrahydropyran (94 mg, 0.56 mmol) were dissolved in 5mL 31 DMF, and then the solution was added with 25 K2CO3 (78 mg, 0.56 mmol) and reacted at 90C for 40 h. After the reaction finished, the mixture was poured into water and extracted with EtOAc (40 mL¡Á3). The ethyl acetate layers were combined and washed with water and saturated salt solution, then dried over anhydrous sodium sulfate and filtered, and the filtrate was vacuum concentrated to give a crude product, which was purified by a preparation plate to give Compound 3a-rac (65 mg, 56.1% yield)., 25637-16-5

25637-16-5 4-Bromotetrahydropyran 13349654, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Ginkgo Pharma Co., Ltd.; CHEN, Li; ZHAI, Peibin; SHAO, Qing; WU, Jin; LI, Xiaowen; (46 pag.)EP3492467; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

a) 4-(p-Tosyloxy)tetrahydro-2H-pyran To an ice-cooled solution of tetrahydro-2H-pyran-4-ol (15g, 0.147mol) in dichloromethane (200ml) was added pyridine (36ml, 0.441mol) followed by 4-methylbenzenesulfonyl chloride (56g, 0.294mol), portionwise. The resultant mixture was stirred at room temperature overnight. After this time, the mixture was partitioned between 2N aqueous hydrochloric acid solution and dichloromethane. The aqueous portion was further extracted with dichloromethane and the organic fractions were combined and washed with brine. After drying over sodium sulphate and filtration, the solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel using a gradient elution with diethyl ether:hexane (50:50, by volume) changing to diethyl ether:hexane (100:0, by volume). This produced the title compound as a colourless oil which solidified upon scratching the walls of the flask (30.3g). LRMS m/z = 274.4 (m+ NH4)+ 1H-NMR (CDCl3): delta =1.6-1.9 (m,4H), 2.4 (s,3H), 3.4-3.5 (m,2H), 3.8-3.9 (m,2H), 4.6-4.7 (m,1H), 7.2-7.4 (m,2H), 7.7-7.8 (m,2H)., 2081-44-9

2081-44-9 Tetrahydro-2H-pyran-4-ol 74956, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Pfizer Limited; PFIZER INC.; EP962457; (1999); 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.14774-37-9,Tetrahydropyran-4-methanol,as a common compound, the synthetic route is as follows.

14774-37-9, To a solution of 97 g (810 mmol) of Compound 6 (190 mL) are added 165 mL of 50% aqueous NaOH solution. To this stirred suspension is added dropwise with cooling a solution of p-toluene-sulfonylchloride (283 g, 1.46 mol) in 2-methyltetrahydrofuran (280 mL). The reaction is stirred at 30-35 C. for 18 h. The suspension is poured into a mixture of ice-water (280 mL) and aqueous HCl solution (37%, 203 mL). After addition of methylcyclohexane (1.4 L) and further ice-water (0.2 L), the reaction mixture is stirred for 2 h in an ice-bath. The resulting crystalline precipitate is isolated by filtration and washed with methylcyclohexane (0.5 L) and water (0.5 L). Drying under reduced pressure at 40 C. gave 216 g of Compound 7 as white crystalline solid. Yield: 99%, ES-MS: m/z 271 [M+H]; 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.19-1.35 (2H, m), 1.54-1.63 (2H, m), 1.85-2.02 (1H, m), 2.45 (3H, s), 3.28-3.39 (2H, m), 3.86 (2H, d, J=6.60 Hz), 3.93 (2H, dd, J=11.37, 4.52 Hz), 7.35 (2H, d, J=9.29 Hz), 7.78 (2H, d, J=8.31 Hz).

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; US2011/71196; (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.127956-11-0,Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate,as a common compound, the synthetic route is as follows.

Example 204B 3,3-Dimethyl- l,5,9-trioxa-spiro[5.5]undecane-7-carboxylic acid methyl ester A mixture of Example 204A (5 g, 31 mmol), 2,2-dimethyl-propane-l,3-diol (4.27 g, 41 mmol) and toluene-4-sulfonic acid (200 mg) in toluene (60 mL) was refluxed overnight using Dean- Stark trap. After cooling to room temperature, the reaction mixture was quenched with a saturated NaHC(? (100 mL) solution. The aqeous layer was extracted with ethyl acetate (200 mL). The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified by column chromatography (petroleum ether/ethyl acetate: 10/2) to provide the title compound (5 g, 65%) as a red oil.

127956-11-0, The synthetic route of 127956-11-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; WANG, Xueqing; MEYER, Michael; YAO, Betty; GUO, Tao; WEI, Guo Ping,Robert; WANG, Lijuan, Jane; WO2013/10453; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

137052-08-5, 1-(Tetrahydro-2H-pyran-4-yl)ethanone is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a 100-mL round-bottom flask was placed a solution of 1-(tetrahydro-2H-pyran-4-yl)ethan-1-one (10 g,78.0 mmol) in THF (200 mL) then the solution was cooled to 0C and NaBH4 (1.50 g,39.5 mmol) was added. The reaction was stirred for 30 mm at 0C,quenched by the addition of water,and extracted withEtOAc. The organic extracts were combined and concentrated under reduced pressure affording 10 g (98%) of the title compound as colorless oil. Mass Spectrum (LCMS,ESI pos):Calcd. for C7H15O2: 131.1 (M+H); Found: 131.2.

137052-08-5, 137052-08-5 1-(Tetrahydro-2H-pyran-4-yl)ethanone 9877365, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; PROTEOSTASIS THERAPEUTICS, INC.; MUNOZ, Benito; BASTOS, Cecilia, M.; PARKS, Daniel; KOMBO, David; (301 pag.)WO2017/62581; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics