Category: 137052-08-5

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.137052-08-5,1-(Tetrahydro-2H-pyran-4-yl)ethanone,as a common compound, the synthetic route is as follows.

Combine selenium dioxide (181.80 g, 1.64 mol), 1,4-dioxane (630 mL), acetic acid (31.5 mL, 0.67 eq), and water (31.5 mL). Heat to 90C and add l-(tetrahydro-pyran- 4-yl)-ethanone (105.0 g, 1.0 eq) dropwise. Stir at 90C overnight. After cooling, filter through a plug of silica/Celite and wash with tetrahydrofuran (2.5 L). Dry the organics over anhydrous magnesium sulfate, filter, and concentrate in vacuo. Dissolve the crude material in methanol (500 mL) and add to a solution of tert-butyl 4-formylpiperidine- 1 – carboxylate (174.72 g, 1.0 eq) and ammonium acetate (315.74 g, 5.0 eq) in methanol(1.45 L) at 0C. Stir overnight. Filter through silica/Celite and wash with ethyl acetate and methanol. Concentrate the filtrate in vacuo. Dilute with methyl tert-butyl ether (400 mL) and water (400 mL), then adjust the pH to 2 by addition of aqueous 85% phosphoric acid. Separate the layers and wash the aqueous phase with methyl tert-butyl ether (200 mL). Basify the resulting aqueous phase with solid sodium carbonate to pH 10 and extract with ethyl acetate (3 x 200 mL). Wash the organics with saturated aqueous sodium chloride. Dry the organics over anhydrous magnesium sulfate, filter, and concentrate in vacuo to afford tert-butyl 4-(4-(tetrahydro-2H-pyran-4-yl)-lH-imidazol-2- yl)piperidine- 1-carboxylate (105.1 g, 38%). MS (ES) m/z = 336 [M]+., 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; ELI LILLY AND COMPANY; BEIGHT, Douglas, Wade; BURKHOLDER, Timothy, Paul; CLAYTON, Joshua, Ryan; EGGEN, MariJean; HENRY, Kenneth, James, Junior; JOHNS, Deidre, Michelle; PARTHASARATHY, Saravanan; PEI, Huaxing; REMPALA, Mark, Edward; SAWYER, Jason, Scott; WO2011/50016; (2011); 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

General procedure: General Procedure: All catalytic hydrogenation experiments using molecular hydrogen were carried out in a Parr Instruments autoclave (300 mL) advanced with an internal alloy plate include up to 8 uniform reaction vials (4 mL) equipped with a cap and needle penetrating the septum. Representative experiment: Under an argon atmosphere, a vial was charged with Manganese Complex of example 2.1 and base which were dissolved in 2 mL of dried solvent. The resulting red solution was stirred briefly before the ketone or ketoester (0.5 or 1 mmol) was added. The vial was placed in the alloy plate which was then placed into the autoclave. Once sealed, the autoclave was purged 5 times with hydrogen, then pressurized to 30 bar and heated to desired temperature. Afterwards, the autoclave was cooled to RT, depressurized, and the reaction mixture was analyzed by GC-FID or HPLC as well as GC-MS. Product isolation was performed via column chromatography using silica gel as stationary phase and w-pentane / ethylacetate or w-pentane / acetone mixture as eluent. Individual reaction conditions: [a] 2 mol cat., 5 mol NaOiBu, 0.5 mmol substrate, 30 bar, 3h, 50 C, EtOH (1,5 mL) [b] 2 mol cat., 5 mol NaOiBu, 0.5 mmol substrate, 30 bar, 3h, 70 C, EtOH (1,5 mL) [c] 2 mol% cat., 5 mol% NaOiBu, 0.5 mmol substrate, 30 bar, 3h, 50 C, toluene (1,5 mL) [d] 2 mol% cat., 5 mol% NaOiBu, 0.5 mmol substrate, 30 bar, 3h, 50 C, z’PrOH (1,5 mL) [e] 2 mol% cat., 5 mol% NaOiBu, 0.5 mmol substrate, 30 bar, 3h, 50 C, /PrOH (1,5 mL) [f] 1 mol% cat., 5 mol% KOiBu, 0.5 mmol substrate, 30 bar, 4-5h, 40 C, tert-amyl alcohol (1,5 mL) [g] 1 mol% cat., 5 mol% KOiBu, 0.5 mmol substrate, 30 bar, 16h, 50 C, toluene (1,5 mL) [h] 2 mol% cat., 5 mol% KOiBu, 0.5 mmol substrate, 30 bar, 8h, 100 C, dioxan (1,5 mL) [i] 1 mol% cat., 5 mol% KOiBu, 1 mmol substrate, 30 bar, 4h, 30 C, 1,4-dioxane (2 mL) [j] 1 mol% cat., 5 mol% KOiBu, 1 mmol substrate, 30 bar, 4h, 40 C, tert-amyl alcohol (2 mL) [k] 1 mol% cat., 5 mol% KOiBu, 1 mmol substrate, 30 bar, 4h, 80 C, tert-amyl alcohol (2 mL) [1] 2 mol% cat., 5 mol% KOiBu, 1 mmol substrate, 30 bar, 4h, 50 C, toluene (2 mL) [m] 2 mol% cat., 5 mol% KOiBu, 1 mmol substrate, 30 bar, 4h, 80 C, tert-amyl alcohol(2 mL) [n] 2 mol% cat., 5 mol% NaOiBu, 0.5 mmol substrate, 30 bar, 3h, 70 C, PrOH (1,5 mL) [o] 2 mol% cat., 5 mol% NaOiBu, 0.5 mmol substrate, 30 bar, lh, 50 C, /PrOH (1 mL) SP = side product (Hydrogenation of double bond) Table 1:, 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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BACHMANN, Stephan; BELLER, Matthias; GARBE, Marcel; JUNGE, Kathrin; SCALONE, Michelangelo; (41 pag.)WO2018/189060; (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.137052-08-5,1-(Tetrahydro-2H-pyran-4-yl)ethanone,as a common compound, the synthetic route is as follows.

Step 3 A 200 mL sealed tube was charged with 4-acetyltetrahydro-4H-pyran 3 (7.0 g, 55 mmol), THF (100 mL), and a solution of titanium(IV) ethoxide (28.6 mL, 136 mmol) in THF (30 mL). The resulting mixture was degassed by evacuation and back-fill with N2 (3*), sealed, and immersed in a 85 C. oil bath. After 30 h, the reaction was poured into an erlenmeyer containing 300 mL of water, and the mixture was further diluted with EtOAc (200 mL) and stirred vigorously for 15 minutes. The mixture was then filtered through paper with copious EtOAc washes. The phases of the filtrate were separated and the aqueous portion was extracted 2* with EtOAc. The organic portions were combined, washed with brine, dried over MgSO4, filtered, and concentrated. This crude sample was subjected to column chromatography (ISCO, 330 g silica, 100 mL/min, 0% to 100% EtOAc/hexanes) to give (R)-2-methyl-N-(1-(tetrahydro-2H-pyran-4-yl)ethylidene)propane-2-sulfinamide 4 (9.2 g, 73%). LCMS (conditions D): tR=1.85 min, m/e=232.2 (M+H, base).

137052-08-5, The synthetic route of 137052-08-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Schering Corporation; US2012/195881; (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.137052-08-5,1-(Tetrahydro-2H-pyran-4-yl)ethanone,as a common compound, the synthetic route is as follows.

To a solution of 1-tetrahydro-2H-pyran-4-ylethanone (166mg, 1.30 mmol) in MeOH (7.5 mL) hydrazine hydrate (55-60% in water, 0.90 mL, 17.61 mmol) was added. Thereaction mixture was heated to refluxforl6 h, cooled andconcentrated under reduced pressure to give crude 1-tetrahydropyran-4-ylethanone hydrazone (171 mg, 1.20 mmol, 93% yield) as a colourless oil. 1H NMR (400 MHz, CDCI3, ): 4.92 (5, 2H), 4.03-3.98 (m, 2H), 3.45-3.40 (m, 2H), 2.38-2.30 (m, 1H), 1.73 (5, 3H), 1.65-1.63 (m, 4H)., 137052-08-5

The synthetic route of 137052-08-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; REDX PHARMA PLC; GUISOT, Nicolas; (266 pag.)WO2017/103611; (2017); 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

A solution of 1-tetrahydro-2H-pyran-4-ylethanone (351 mg; 2.74 mmol), intermediate11(600 mg; 1.83 mmol), Ti(OiPr)4 (870 jiL; 2.92 mmol) in EtOH (3 mL) was stirred for2 hours at 45C. Additional EtOH (18 mL) and NaBH4 (138 mg; 3.65 mmol) were added.The reaction mixture was stirred at room temperature for 5 hours. The reaction mixturewas diluted with DCM and poured onto a 10% aqueous solution of K2C03. The insolublematerial was removed by filtration over celite. The organic layer was separated, washedwith water, dried over MgSO4, filtered and evaporated to dryness. The residue waspurified by chromatography over silica gel (irregular SiOH, 24g; mobile phase : gradientfrom 0% NH4OH, 0% MeOH, 100% DCM to 1% NH4OH, 10% MeOH, 90% DCM).The fractions containing the product were collected and evaporated to dryness yielding487 mg (60%) of compound 145. The enantiomers of compound 145 were separated bychiral SFC (CHIRALPAK AD-H 5.im 250*30mm; mobile phase: 70% C02, 30%mixture of EtOH/iPrOH 50/50 v/v). The fractions containing the products were collectedand evaporated to dryness. The residues were freeze dried from from water/ACN (80/20;10 mL)yielding 171mg (21%) of compound 154 and 178mg (22%) of compound 155.

137052-08-5, The synthetic route of 137052-08-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; PANDE, Vineet; HERKERT, Barbara; KROSKY, Daniel, Jason; QUEROLLE, Olivier, Alexis, Georges; PILATTE, Isabelle, Noelle, Constance; PATRICK, Aaron, Nathaniel; (250 pag.)WO2018/50686; (2018); 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

Example 16. Synthesis of 3-fluoro-2-(5-oxo-4-(3-(tetrahydro-2H-pyran-4-yl)-lH- razol- l-yl)-6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-2-yl)benzonitrile, I- 16 16.4 1-16 Synthesis of compound 16.2. Solution of 16.1 (0.5g, 3.9mmol, leq) in DMF-DMA (5 niL) was heated to 100 C for 16h. Upon completion of the reaction was reaction, solvents were removed under reduced pressure to get crude 16.2 (0.45g, 62.95%), MS(ES): m/z 184.12 [M+H]+. The crude product was used in to next step without further purification., 137052-08-5

As the paragraph descriping shows that 137052-08-5 is playing an increasingly important role.

Reference£º
Patent; NIMBUS LAKSHMI, INC.; MASSE, Craig E.; GREENWOOD, Jeremy Robert; ROMERO, Donna L.; HARRIMAN, Geraldine C.; WESTER, Ronald T.; SHELLEY, Mee; KENNEDY-SMITH, Joshua Jahmil; DAHLGREN, Markus; MONDAL, Sayan; (342 pag.)WO2017/40757; (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.137052-08-5,1-(Tetrahydro-2H-pyran-4-yl)ethanone,as a common compound, the synthetic route is as follows.

General procedure: To the mixture of sodium ethanolate (21% solution in ethanol, 9.898 ml, 26.52 mmol) in ethanol (20 ml) at 0C 1 -(tetrahydro-2H-pyran-4-yl)ethanone (Intermediate P20, 2.000 g, 15.60 mmol) and diethyl oxalate (3.916 g, 26.52 mmol) were added consecutively. The whole was stirred for 1 hours at 0C, then for 2 hours at room temperature. The mixture was added with 30 ml of water and acidified with 6M hydrochloric acid to pH = 3. Aqueous layer was extracted with ethyl acetate ( 3 x 50 ml). Organic layer was dried over sodium sulphate. Solvent and drying agent were removed to obtain 5.056 g of the title product, which was used without purification for further reactions. MS-ESI (m/z) calculated for CnHi604Na [M+Na]+: 251.09, determined 251.1

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; CELON PHARMA S.A.; MOSZCZYNSKI-PETKOWSKI, Rafal; BOJARSKI, Lukasz; MAJER, Jakub; WIECZOREK, Maciej; DUBIEL, Krzysztof; LAMPARSKA-PRZYBYSZ, Monika; WO2014/24125; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics