2-Aminopropanol → HCID 18317565, compound

Temperature

150 °C

A mixture of 5-phenylcyclohexane-1,3-dione (4.0 g), 2-aminopropanol (2.1 g), molecular sieves 4A (24 g) and tetrahydrofuran (60 ml) was refluxed for 14 hours and cooled, and insoluble materials were filtered off. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in dimethylformamide (100 ml). To the solution were added 2-bromomesitylene (4.2. g), tetrakistriphenylphosphine palladium (0.6 g) and potassium carbonate (5.9 g), and the mixture was stirred at 150° C. for 3.5 hours and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (EtOAc), and the resulting crystals were recrystallized from ethyl acetate-hexane to give colorless crystals of 2-methyl-6-phenyl-4,5,6,7-tetrahydroindol-4-one (3.2 g).

1. temperaturewas refluxed for 14 hours
2. temperaturecooled
3. filtrationinsoluble materials were filtered off
4. customUnder reduced pressure, the solvent was evaporated
5. dissolutionthe residue was dissolved in dimethylformamide (100 ml)
6. additionTo the solution were added 2-bromomesitylene (4.2. g), tetrakistriphenylphosphine palladium (0.6 g) and potassium carbonate (5.9 g)
7. concentrationconcentrated under reduced pressure
8. dissolutionThe residue was dissolved in ethyl acetate
9. washthe solution was washed with water and saturated brine
10. dry with materialdried with magnesium sulfate
11. concentrationconcentrated under reduced pressure
12. customThe residue was purified with silica gel column chromatography (EtOAc)
13. customthe resulting crystals were recrystallized from ethyl acetate-hexane

ORD record

ord-b83cb33303c94c76b1866070e05473cc

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06350749B1