With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1172623-99-2,tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.
Step 6: Ru Oxidation to Provide 9; To a solution of the alcohol 8 (40.0 g, 121.4 mmol) in CH3CN (120 mL), AcOH (20 mL), and H2O (20 mL) was added a solution of RuCl3 (50.4 mg, 0.243 mmol) in H2O (40 mL) at 0 C. NaBrO3 (9.2 g, 60.7 mmol) was added in portions at 0 C. The resulting reaction mixture was stirred at 0 C. until a complete consumption of alcohol 8 was achieved by HPLC. H2O (600 mL) was added dropwise over 5 h at 0 C. The slurry was aged overnight at 0 C. The product was collected by filtration, washed with CH3CN/H2O=1/9 (200 mL¡Á2), and dried under vacuum to give 9. 9 has two rotomers in DMSO in about a 4:1 ratio at ambient temperature. For the major rotomer of 9: 1H NMR (500 MHz, DMSO-d6): delta 7.27 (m, 1H), 7.20 (m, 2H), 7.12 (d, J=9.2 Hz, 1H), 4.76 (d, J=9.5 Hz, 1H), 4.19 (d, J=16.1H), 4.10 (d, J=16.1 z, 1H), 4.05 (m, 1H), 2.76 (dd, J=16.4, 6.2 Hz, 1H), 2.71 (dd, J=16.4, 10.1 Hz, 1H), 1.20 (s, 9H). 13C-NMR (125 MHz, d6-DMSO): delta 205.4, 158.0 (d, J=236.9 Hz), 156.2 (dd, J=241.8, 1.8 Hz), 154.2, 127.8 (dd, J=16.0, 8.0 Hz), 116.6 (dd, J=25.2, 8.0 Hz), 116.2 (dd, J=23.4, 8.0 Hz), 115.2 (dd, J=24.0, 3.1 Hz), 77.9, 74.5, 73.6, 50.6, 44.1, 27.9.
The synthetic route of 1172623-99-2 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; Xu, Feng; Kim, Mary M.; Kohmura, Yoshinori; Sladicka, Tricia; Rosen, Jonathan D.; Zacuto, Michael J.; US2009/187028; (2009); A1;,
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