反应详情

温度

70 °C

To compound 45C (2.08 g, 3.42 mmol) in MeOH (50 mL) and THF (20 mL) was added NaBH4 (0.259 g, 6.83 mmol). The reaction mixture was heated at 70° C. for 2 hours. The solvent was removed, and the residue was partitioned between EtOAc and water. The organic layer was isolated, and the aqueous layer was extracted with additional EtOAc. The combined organic layers were washed with brine, dried over MgSO4, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel eluting with 1:1/hexanes:EtOAc to provide 1.86 g of the desired product: 1H NMR (DMSO-d6): δ 8.24-8.26 (m, 1H), 7.94 (d, J=7.67 Hz, 1H), 7.70 (d, J=8.20 Hz, 1H), 7.52-7.56 (m, 1H), 7.34-7.42 (m, 3H), 6.00 (s, 2H), 5.77 (t, J=5.52 Hz, 1H), 5.13 (s, 2H), 4.83 (d, J=5.52 Hz, 2H), 3.67-3.75 (m, 7H), 3.03 (t, J=5.98 Hz, 2H), 0.87-0.91 (m, 2H), −0.18 (s, 9H). MS (ESI(+)): m/z 611 (M+H).

1. customThe solvent was removed
2. customthe residue was partitioned between EtOAc and water
3. customThe organic layer was isolated
4. extractionthe aqueous layer was extracted with additional EtOAc
5. washThe combined organic layers were washed with brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated under reduced pressure
8. customThe crude material was purified by column chromatography on silica gel eluting with 1:1/hexanes