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

HRID 1434548Notes

Reaction equation

HRID 1434548 reaction equation
C1C2C(=CC=CC=2)[C@H](N)[C@@H]1O.[NH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][C:20](=[O:23])[CH2:19][CH2:18]2.[OH-].[K+]>C(O)(C)C.C1C=CC=CC=1.Cl[Ru]Cl>[NH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]2

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 9866743(1S,2R)-(-)-1-Amino-2-indanolHCID 230669938-Amino-3,4-dihydro-1H-naphthalen-2-one

Product 1

HCID 57936087(2R)-8-Amino-1,2,3,4-tetrahydro-2-naphthalenolYield 56%

Reagents, catalysts & solvents 2

HCID 11096978HCID 11096978, compoundCatalystHCID 3776IsopropanolSolvent3×

Procedure

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 pressure, 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).

Workup

  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 pressure
  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

Sources & evidence

ORD record
ord-827d7bfa5e734221a2f75eb168c667f2
Source dataset
uspto-grants-2009_11
Patent number
US07615557B2

Reaction notes

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