Category: 14774-36-8

14774-36-8, (Tetrahydropyran-3-yl)methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of (tetrahydro-2H-pyran-3-yl)methanol (1 g, 8.621 mmol, commercial source: Frapps) in Dichloromethane (20 mL), thionyl chloride (1 mL, 13.785 mmol, commercial source: Avra) was added slowly at 0 C and then stir at 26 C for 16 h. Upon completion, the reaction mixture was evaporated under reduced pressure, diluted with saturated NaHCC>3 solution (50 mL) and extracted with dichloromethane (3×50 mL).The combined organic solution was dried over anhydrous Na2S04, filtered and the filtrate was concentrated under reduced pressure to afford 3-(chloromethyl)tetrahydro-2H-pyran (300 mg).1H NMR (400 MHz, DMSO-d6) delta 3.90- 3.73 (m, 4H), 3.35-3.20 (m, 2H), 1.90-1.81 (m, 1 H), 1 .77-1 .50 (m, 2H), 1.35-1.17 (m, 2H).

14774-36-8, As the paragraph descriping shows that 14774-36-8 is playing an increasingly important role.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ALEMPARTE-GALLARDO, Carlos; ENCINAS, Lourdes; ESQUIVIAS PROVENCIO, Jorge; (206 pag.)WO2019/34729; (2019); 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.14774-36-8,(Tetrahydropyran-3-yl)methanol,as a common compound, the synthetic route is as follows.

[00175] At rt, to a suspension of 4,5-dichloro-3,6-dioxocyclohexa-1 ,4-diene-1 ,2- dicarbonitrile (1 .216 g, 5.356 mmol), TBAB (1 .727 mg, 5.356 mmol) and PPh3 (1 .405 g, 5.356 mmol) in DCM (15 mL) was added a solution of 15.1 (360 mg, 3.151 mmol) in DCM (10 mL) dropwise quickly. After addition, the reaction mixture turned to a brown solution and was stirred at rt for another 1 h. Then it was purified by column chromatography on silica gel (pH=8~9, eluent: PE/EA=10:1) directly to give crude title compound (140 mg, 25%) as a colorless oil.

14774-36-8, As the paragraph descriping shows that 14774-36-8 is playing an increasingly important role.

Reference£º
Patent; NOVARTIS AG; HE, Feng; DU-CUNY, Lei; XIAO, Qitao; XUN, Guoliang; ZHENG, Qiangang; (152 pag.)WO2017/149463; (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.14774-36-8,(Tetrahydropyran-3-yl)methanol,as a common compound, the synthetic route is as follows.

14774-36-8, To a solution of Compound 29 (100 mg, 0.34 mmol) in THF (4 mL) was added (0759) tetrahydropyran-3-ylmethanol (117.65 mg, 1.01 mmol), PPli3 (177.1 mg, 0.68 mmol) and then DIAD (136.54 mg, 0.68 mmol). The resulting mixture was stirred at 20 C under N2 for 16 hours . The reaction solution was concentrated to give the crude product, which was purified by flash chromatography on silica gel (EtOAc in PE = 0% to 10% to 20%) and Prep- TLC (silica gel, PE: EtOAc = 4: 1) to afford A-58 (50 mg) as a solid. A-58 was purified by SFC (Chiralcel AD (250 mm x 30 mm, 5 muiotaeta); A = C02 and B = EtOH (0.1% NH3H20); 38C; 50 mL/min; 30% B over 11 minutes; multiple injections) to afford Enantiomer 1, randomly assigned as Compound 66 (Rt = 6.8 min) and Enantiomer 2, randomly assigned as Compound 67 (Rt = 9.2 min). Compound 66 (14.37 mg, 0.04 mmol) 1H NMR (CDCI3 400MHz) deltaEta = 8.00 (d, 2H), 7.48 (s, 2H), 7.33 (d, 2H), 4.01 – 3.80 (m, 4H), 3.56 – 3.35 (m, 2H), 2.43 – 2.30 (m, 1H), 1.96 – 1.85 (m, 1H), 1.82 – 1.72 (m, 1H), 1.69 – 1.59 (m, 1H), 1.49 – 1.37 (m, 1H). LCMS Rt = 1.32 min using Method A, MS ESI calcd. for Ci9Hi8F3N204 (0760) [M+H]+ 395.1, found 395.0. Compound 67 (15.66 mg, 0.04 mmol) 1H NMR (CDC13, 400MHz) deltaEta = 8.00 (d, 2H), 7.48 (s, 2H), 7.33 (d, 2H), 4.00 – 3.81 (m, 4H), 3.55 – 3.46 (m, 1H), 3.41 (dd, 1H), 2.43 – 2.31 (m, 1H), 1.96 – 1.86 (m, 1H), 1.82 – 1.72 (m, 1H), 1.69 – 1.59 (m, 1H), 1.49 – 1.37 (m, 1H). LCMS Rt = 1.33 min using Method A, MS ESI calcd. for Ci9Hi8F3N204 [M+H]+ 395.1, found 395.1.

14774-36-8 (Tetrahydropyran-3-yl)methanol 85769, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

14774-36-8, (Tetrahydropyran-3-yl)methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 85: Tetrahydro-2H-pyran-3-ylmethyl methanesulfonateTo tetrahydro-2H-pyran-3-ylmethanol (4.92g) in dry dichloromethane (140 ml) at O0C and under nitrogen, was added anhydrous triethylamine (13.6 ml) in one go, followed by mesyl chloride (4.3 ml) dropwise over 5 minutes. The reaction was allowed to warm to room temperature and stirred at this temperature overnight. The reaction was quenched with saturated aqueous sodium bicarbonate (50 ml). The organic layer was separated, passed through a hydrophobic frit to dry and concentrated in vacuo to yield a red oil (8.8 g).1H NMR (CDCI3): delta 4.18-4.08 (2H, m), 3.94-3.88 (1 H, m), 3.81 (1 H, m), 3.51-3.43 (1 H, m), 3.37-3.31 (1 H, m), 3.01 (3H, s), 2.07 (1 H, m), 1.85 (1 H, m), 1.72-1.56 (2H, m), 1.47-1.36 (1 H, m).

14774-36-8, The synthetic route of 14774-36-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/101867; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

14774-36-8, (Tetrahydropyran-3-yl)methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

14774-36-8, To the mixture of Compound 5 (150 mg, 0.51 mmol), DIAD (184.94 mg, 0.91 mmol) and tetrahydropyran-3-ylmethanol (106.24 mg, 0.91 mmol) in THF (5 mL) was added PPh3 (239.89 mg, 0.91 mmol). The mixture was stirred at 20 C for 16 hours under N2. The mixture was concentrated, and the residue was diluted with sat.NH4Cl (20 mL), and extracted with EtOAc (20 mL x 2). The combined organic phase was washed with brine (10 mL), dried over Na2S04 and filtered, and the filtrate was concentrated to give a residue that was purified by Prep-HPLC (Xtimate C18 (250 mm x 50mm, 10 muiotaeta) A = H20 (10 mM % NH3HCO3) and B = CH3CN); 55-85 %B over 11.3 minutes) to afford Compound 72 (52.87 mg, 0.13 mmol) as an oil. *H NMR (CD3CN 400MHz) deltaH = 7.73 (d, 2H), 7.42 – 7.35 (m, 4H), 7.33 – 7.27 (m, 1H), 3.83 – 3.69 (m, 4H), 3.43 (dt, 1H), 3.34 – 3.26 (m, 1H), 2.24 – 2.15 (m, 1H), 1.89 – 1.80 (m, 1H), 1.73 – 1.64 (m, 1H), 1.58 – 1.46 (m, 1H), 1.46 – 1.34 (m, 1H). LCMS Rt = 1.293 min using Method A, MS ESI calcd. for C20H19F3NO4 [M+H]+ 394.1, found 394.1.

The synthetic route of 14774-36-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

14774-36-8, (Tetrahydropyran-3-yl)methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

169a) 3-((3-Bromophenoxy)methyl)tetrahydro-2H-pyran A solution of 3-bromophenol (500 mg, 2.89 mmol), triphenylphosphine (758 mg, 2.89 mmol) and (tetrahydro-2H-pyran-3-yl)methanol (420 mg, 3.62 mmol) in tetrahydrofuran (THF) (10 mL) was added DIAD (0.674 mL, 3.47 mmol) in tetrahydrofuran (THF) (10 mL) slowly under nitrogen at 0C. The reaction mixture was stirred at 25 C for 16 h. The solvent was evaporated and was purified by reverse-phase HPLC to obtain the title compound 3-((3-bromophenoxy)methyl)tetrahydro-2H-pyran (260 mg, 0.91 1 mmol, 31 .5 % yield). LC-MS m/z 271 .0(M+H)+, 2.10 min (ret. time)., 14774-36-8

14774-36-8 (Tetrahydropyran-3-yl)methanol 85769, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; CALLAHAN, James Francis; KERNS, Jeffrey K.; LI, Peng; LI, Tindy; MCCLELAND, Brent W.; NIE, Hong; PERO, Joseph E.; DAVIES, Thomas Glanmor; GRAZIA CARR, Maria; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; NORTON, David; VERDONK, Marinus Leendert; WOOLFORD, Alison Jo-Anne; WILLEMS, Hendrika Maria Gerarda; (664 pag.)WO2017/60854; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics