反应详情

To a solution of 1.0 g (2.52 mmol) of 2-benzyl-6,7-dimethoxy-4-phenyl-2,3,4,5-tetrahydro-1H-benz[e]isoindole, from Step 5, in 22 mL of 1,2-dichloroethane was added 0.11 g (0.05 mmol) of 1,8-bis(dimethylamino)-naphthalene and 0.33 mL (3.15 mmol) of 1-chloroethyl chloroformate at 0° C. The solution was heated to reflux for 2 h and the solvent removed in vacuo. The residue was filtered through silica gel eluted with 25% ethyl acetate in hexanes. After concentration under reduced pressure, methanol (20 mL) was added and the solution was heated to reflux for 30 minutes, before the solvent was removed in vacuo. The product was crystallized from ethanol/ether to give 0.46 g. (75% yield) of 6,7-dimethoxy-4-phenyl-2,3,4,5-tetrahydro-1H-benz[e]isoindole hydrochloride as a white solid.; MS DCI: 308 (M+H)+ ; 1H NMR (d6 -DMSO) δ: 3.05-3.25 (m, 2H), 3.55 (s, 3H), 3.80 (s, 3H), 3.88 (m, 1H), 4.0-4.15 (m, 2H), 4.25-4.45 (m, 2H), 6.91 (m, 1H), 7.15-7.3 (m, 3H), 7.4-7.6 (m, 3H).

1. temperatureThe solution was heated
2. temperatureto reflux for 2 h
3. customthe solvent removed in vacuo
4. filtrationThe residue was filtered through silica gel
5. washeluted with 25% ethyl acetate in hexanes
6. concentrationAfter concentration under reduced pressure, methanol (20 mL)
7. additionwas added
8. temperaturethe solution was heated
9. temperatureto reflux for 30 minutes, before the solvent
10. customwas removed in vacuo
11. customThe product was crystallized from ethanol/ether
12. customto give 0.46 g