With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1768-64-5,4-Chlorotetrahydropyran,as a common compound, the synthetic route is as follows.
A solution of 4-chlorotetrahydro-2H-pyran (1.2 g, 10 mmol) in THF (5 mL) was added dropwise to a mixture of Mg (486 mg, 20 mmol) and I2 (1 mg) at 70oC. The mixture was stirred at 50oC for 0.5 h, diluted with THF (5 mL) and used directly. To a solution of (tetrahydro-2H- pyran-4-yl)magnesium chloride (4.14 mL, 1 M in THF) was added N-8-7_1 (500 mg, 1.38 mmol) in THF (5 mL) at 0C under N2. Then the mixture was stirred at 15oC for another 18 hrs. The reaction mixture was quenched with sat. NH4Cl (5 mL), and the resulting mixture was extracted with EtOAc (2 x 10 mL). The combined organic layer was washed with brine (5 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash column (0-15% EtOAc in PE) to give N-8-17_1 (350 mg, 57%) as a solid. 1H NMR (400 MHz, CDCl3) delta 4.08-3.91 (m, 2H), 3.43-3.31 (m, 2H), 3.31-3.25 (m, 1H), 1.98- 1.91 (m, 2H), 1.91-1.80 (m, 1H),1.70-1.50 (m, 10H), 1.50-1.41 (m, 2H), 1.41-1.32 (m, 5H), 1.32-1.15 (m, 9H), 1.15-0.92 (m, 6H), 0.92-0.83 (m, 7H), 0.65 (s, 3H) .
The synthetic route of 1768-64-5 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; SAGE THERAPEUTICS, INC.; SALITURO, Francesco, G.; ROBICHAUD, Albert, J.; MARTINEZ BOTELLA, Gabriel; HARRISON, Boyd, L.; GRIFFIN, Andrew; LA, Daniel; (299 pag.)WO2018/75698; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics