Potassium Hydroxide → (2R)-8-Amino-1,2,3,4-tetrahydro-2-naphthalenol

A stirred solution benzeneruthenium(II) chloride dimmer (1.55 g) and (1S, 2R)-(−)-cis-1-amino-2-indanol (1.85 g) in degassed isopropanol (500 ml) was heated at 80° C. for 20 minutes under argon, and then cooled to room temperature. The mixture was added to the solution of 8-amino-3,4-dihydro-1H-naphthalen-2-one (25.0 g) in isopropanol (700 ml) at room temperature followed by the prepared solution of potassium hydroxide (1.74 g) in 300 ml of isopropanol (pre-prepared at 45° C. to dissolve and then cooled to room temperature). After stirred at 45° C. for 30 minutes, the mixture was cooled to room temperature and was passed through silica gel pad and washed with ethylacetate. The filtrate was concentrated under reduced pressures and the obtained solid was dissolved in dichloromethane and treated with activated charcoal for 10 minutes. After filtered through a silica gel pad, the mixture was concentrated under reduced pressure. The obtained product was recrystallized from dichloromethane to afford red crystal, of (R)-8-amino-1,2,3,4-tetrahydro-naphthalen-2-ol (14 g, 56% yield).

1. custompre-prepared at 45° C.
2. dissolutionto dissolve
3. temperaturecooled to room temperature)
4. temperaturethe mixture was cooled to room temperature
5. washwashed with ethylacetate
6. concentrationThe filtrate was concentrated under reduced pressures
7. dissolutionthe obtained solid was dissolved in dichloromethane
8. additiontreated with activated charcoal for 10 minutes
9. filtrationAfter filtered through a silica gel pad
10. concentrationthe mixture was concentrated under reduced pressure
11. customThe obtained product was recrystallized from dichloromethane
12. customto afford red crystal

ORD record

ord-b174e98179204ea480eb6c9eeea13b36

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07612113B2