Water → 6-Methoxy-1,2,3,4-tetrahydroisoquinoline

In methanol (100 ml), 6-methoxy-3,4-dihydroisoquinoline (10.4 g) was dissolved. After the addition of water (10 ml) and then sodium borohydride (6.10 g), the resulting mixture was stirred at room temperature for 15 minutes. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in dichloromethane. The resulting solution was washed with water. The organic layer so separated was dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (dichloromethane˜dichloromethane:methanol=100:15), whereby the title compound (7.95 g, 76%) was obtained.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutionthe residue was dissolved in dichloromethane
3. washThe resulting solution was washed with water
4. customThe organic layer so separated
5. dry with materialwas dried over anhydrous sodium sulfate
6. distillationThe solvent was then distilled off under reduced pressure
7. customThe residue was purified by chromatography on a silica gel column (dichloromethane˜dichloromethane:methanol=100:15), whereby the title compound (7.95 g, 76%)
8. customwas obtained

ORD record

ord-344b694555ce447392c698191f707b29

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06525042B1