反应详情

SMe2 (205 μL, 2.2 mmol) was added dropwise over 5 min. to a refluxing mixture of 1-(phenylsulfonyl)-3,4-dihydropyrrolo[4,3,2-de]isoquinolin-5(1H)-one, Intermediate 2, (225 mg, 0.72 mmol) in dry THF (10 mL) with continuous reflux for 2.5 h. Additional two portions BH3:SMe2 (100 μL×2) were added (2.5 h reflux between the additions). Reflux was continued for 5 h after the last addition, then room temperature over night. The reaction was quenched by addition of HCl in MeOH (1.25 M, 4 mL) and reflux 1 h. The solvent was evaporated and the crude mixture was extracted with DCM (×2) and sat. Na2CO3(aq). The organic layers were combined, dried and concentrated. Purification was performed by flash column chromatography (3-5% MeOH in DCM) which gave 66 mg of the title compound as a beige solid. MS m/z 299 [M+H]+.

1. temperaturewith continuous reflux for 2.5 h
2. temperaturereflux between the additions)
3. temperatureReflux
4. additionafter the last addition
5. waitroom temperature over night
6. customThe reaction was quenched by addition of HCl in MeOH (1.25 M, 4 mL)
7. temperaturereflux 1 h
8. customThe solvent was evaporated
9. extractionthe crude mixture was extracted with DCM (×2) and sat. Na2CO3(aq)
10. customdried
11. concentrationconcentrated
12. customPurification