反应详情

To a solution of (±)-(7-methyl-4-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1-tosyl-1H-indol-5-yl)methanol (Example 52-C) (210 mg, 0.49 mmol), phthalimide (144 mg, 0.98 mmol), and PPh3 (385 mg, 1.47 mmol) in THF (5 mL) was added DIAD (0.29 mL, 1.48 mmol) at 0° C., and then the mixture was stirred at room temperature for 3.5 h. The reaction was then concentrated and partially purified by SiO2 column chromatography (heptane/EtOAc=1/0 to 6/4). A solution of the resulting residue and 4M HCl in dioxane (4 mL) in MeOH (10 mL) was stirred at room temperature for 0.5 h. The reaction mixture was poured into 5% aq. NaHCO3. The basic mixture was extracted with CH2Cl2. The organics extract was washed with H2O and brine, dried over Na2SO4, and then filtered. Concentration of the filtrate gave a residue which was purified by SiO2 column chromatography (heptane/EtOAc=6/4 to 3/7) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 7.76-7.95 (m, 5H), 7.59 (d, J=8.34 Hz, 2H), 7.38 (d, J=8.34 Hz, 2H), 7.06 (d, J=4.04 Hz, 1H), 6.90 (s, 1H), 5.08 (t, J=5.31 Hz, 1H), 4.91 (s, 2H), 4.85 (d, J=5.31 Hz, 2H), 2.38 (s, 3H), 2.33 (s, 3H).

1. concentrationThe reaction was then concentrated
2. custompartially purified by SiO2 column chromatography (heptane/EtOAc=1/0 to 6/4)
3. stirringA solution of the resulting residue and 4M HCl in dioxane (4 mL) in MeOH (10 mL) was stirred at room temperature for 0.5 h
4. additionThe reaction mixture was poured into 5% aq. NaHCO3
5. extractionThe basic mixture was extracted with CH2Cl2
6. extractionThe organics extract
7. washwas washed with H2O and brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. customConcentration of the filtrate gave a residue which
11. customwas purified by SiO2 column chromatography (heptane/EtOAc=6/4 to 3/7)