2-Butanol, 4-amino- → HCID 18317732, compound

Temperature

150 °C

A mixture of 5-phenylcyclohexane-1,3-dione (4.0 g), 4-aminobutan-2-ol (2.5 g), molecular sieves 4A (24 g) and tetrahydrofuran (60 ml) was refluxed for 13 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 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 5 hours and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed with sodium hydrogen carbonate solution, water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (EtOAc/hexane) to give colorless crystals of 3-ethyl-6-phenyl-4,5,6,7-tetrahydroindol-4-one (2.6 g).

1. temperaturewas refluxed for 13 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. concentrationconcentrated under reduced pressure
7. dissolutionThe residue was dissolved in ethyl acetate
8. washthe solution was washed with sodium hydrogen carbonate solution, water and saturated brine
9. dry with materialdried with magnesium sulfate
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified with silica gel column chromatography (EtOAc/hexane)

ORD record

ord-df37625265294c72bbb2778160233865

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06350749B1