Phosphorus pentachloride → 4,4-Dimethyl-1,2,3,4-tetrahydroisoquinolin-1-one

The compound (1.3 g) obtained in step (d) just above was dissolved in diethyl ether(15 ml). Phosphorus pentachloride (1.1 g) was added to the solution. The mixture was stirred at room temperature for 30 min. The solvent was then removed by distillation under the reduced pressure. Glyme (20 ml) and sodium boron hydride (1.1 g) were added to the residue. The mixture was stirred at room temperature for one hr. Water was added to the reaction solution, followed by stirring. The mixture was then extracted with ethyl acetate. The organic layer was then dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=30:1) to give 4,4-dimethyl-3,4-dihydro-2H-isoquinolin-1-one (1.8 g).

1. customThe solvent was then removed by distillation under the reduced pressure
2. additionGlyme (20 ml) and sodium boron hydride (1.1 g) were added to the residue
3. stirringThe mixture was stirred at room temperature for one hr
4. additionWater was added to the reaction solution
5. stirringby stirring
6. extractionThe mixture was then extracted with ethyl acetate
7. dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
8. customThe solvent was then removed by distillation under the reduced pressure
9. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=30:1)

ORD record

ord-10862ceb3e3d4b48b0093670741af5ff

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06583144B2