反应详情

To a suspension of (±)-7-methyl-4-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1-tosyl-5-vinyl-1H-indole (1.8 g, 4.2 mmol) in tert-BuOH (70 mL)/H2O (70 mL) was added AD-mix-alpha (5 g, 4.2 mmol), and then the mixture was stirred at room temperature for 24 h. The reaction was quenched by aq. Na2S2O3, and the whole mixture was stirred for 0.25 h. The mixture was diluted with CH2Cl2 and partitioned. The organic phase was washed with H2O and brine, dried over Na2SO4, filtered and concentrated. The resulting residue was purified by SiO2 column chromatography (CH2Cl2/MeOH=94/6) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 7.84 (d, J=3.79 Hz, 1H), 7.62 (d, J=8.34 Hz, 2H), 7.40 (d, J=8.34 Hz, 2H), 7.18 (s, 1H), 6.95-6.98 (m, 1H), 5.14 (dd, J=3.92, 6.95 Hz, 1H), 4.69-5.03 (m, 3H), 4.52-4.68 (m, 2H), 3.74-3.92 (m, 1H), 3.44-3.55 (m, 1H), 2.46 (s, 3H), 2.34 (s, 3H), 1.34-1.74 (m, 6H).

1. customThe reaction was quenched by aq. Na2S2O3
2. stirringthe whole mixture was stirred for 0.25 h
3. additionThe mixture was diluted with CH2Cl2
4. custompartitioned
5. washThe organic phase was washed with H2O and brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe resulting residue was purified by SiO2 column chromatography (CH2Cl2/MeOH=94/6)