反应详情

温度

0 °C

To a solution of 2-hydroxymethyltetrahydroquinoline (10 g, 61 mmol), imidazole (10.0 g, 147 mmol), and triphenylphosphine (19.0 g, 72.4 mmol) in a mixed solvent of 5:1 toluene/acetonitrile (360 mL) was added iodine (16.85 g, 66.4 mmol) at 0° C. The mixture was stirred for 2 h at 0° C. and aqueous sodium thiosulfate was added. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and concentrated. The residue was triturated with diethyl ether and insoluble materials were removed by filtration. The filtrate was concentrated and the residue was dissolved in DMF (60 mL) and potassium phthalimide (13.6 g, 73.48 mmol) was added. The mixture was heated at 60° C. for 2 h and diluted with water (200 mL). The mixture was extracted with 1:1 toluene/ethyl acetate (200 mL×2). The organic layers were washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified with silica gel column chromatography with 10:1 to 6:1 hexane/ethyl acetate to give 10.25 g of 2-Phthalimidomethyltetrahydroquinoline (75%): 1H NMR (270 MHz, CDCl3) δ7.86 (m, 2H), 7.74 (m, 2H), 6.95 (m, 2H), 6.59 (t, 1H, J=8 Hz), 6.49 (d, 1H, J=8 Hz), 3.91 (dd, 1H, J=14, 5 Hz), 3.78 (dd, 1H, J=14, 5 Hz), 3.68 (m, 1H), 2.78 (m, 2H), 2.00 (m, 1H), 1.69 (m, 1H).

1. customThe organic layer was separated
2. washwashed with water and brine
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated
5. customThe residue was triturated with diethyl ether and insoluble materials
6. customwere removed by filtration
7. concentrationThe filtrate was concentrated
8. dissolutionthe residue was dissolved in DMF (60 mL)
9. temperatureThe mixture was heated at 60° C. for 2 h
10. extractionThe mixture was extracted with 1:1 toluene/ethyl acetate (200 mL×2)
11. washThe organic layers were washed with brine
12. dry with materialdried over magnesium sulfate
13. concentrationconcentrated
14. customThe residue was purified with silica gel column chromatography with 10:1 to 6:1 hexane/ethyl acetate