反应详情

温度

70 °C

(3aR*,4S*,9bR*)-2-Benzyl-6-chloro-3a,4-dimethyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindol-1-one (229 mg, 0.674 mmol) was dissolved in THF (2.6 ml). Borane THF (2 M solution) (6.74 mmol, 6.74 ml) was added and the reaction mixture was heated to 70° C. overnight. MeOH and 5 N aq HCl (4 ml) were then added and the resulting solution was heated at 70° C. for a further 2 hours. The organic solvents were removed in vacuo and the reaction mixture was basified using 4 N NaOH. The aqueous mixture was extracted with DCM (×3) and the combined organic extracts were dried over magnesium sulphate, filtered and concentrated in vacuo to afford a residue that was purified by silica column chromatography (eluting with heptane—heptane: 30% ethyl acetate) to give (3aR*,4S*,9bR*)-2-benzyl-6-chloro-3a,4-dimethyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (52 mg). m/z: 326.3 [M+H]+.

1. temperaturethe resulting solution was heated at 70° C. for a further 2 hours
2. customThe organic solvents were removed in vacuo
3. extractionThe aqueous mixture was extracted with DCM (×3)
4. dry with materialthe combined organic extracts were dried over magnesium sulphate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto afford a residue that
8. customwas purified by silica column chromatography (eluting with heptane—heptane: 30% ethyl acetate)