Potassium Hydroxide → 8-Amino-1,2,3,4-tetrahydronaphthalen-2-ol

HRID 416129Notes

Reaction equation

HRID 416129 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.C1C=CC=CC=1.Cl[Ru]Cl.Cl[Ru]Cl>[NH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][CH: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 230669958-Amino-1,2,3,4-tetrahydronaphthalen-2-olYield 65%

Reagents, catalysts & solvents 2

HCID 10962144Benzeneruthenium(II) Chloride DimerCatalystHCID 3776IsopropanolSolvent3×

Procedure

To a stirred solution of benzeneruthenium(II) chloride dimer (3.10 mg, 0.006 mmol) and (1S, 2R)-(−)-cis-1-amino-2-indanol (3.7 mg, 0.025 mmol) in degaussed iso-propanol was heated at 80° C. for 20 minutes under argon. The mixture was added to the solution of 8-amino-3,4-dihydronaphthalen-2(1H)-one (50 mg, 0.310 mmol) in isopropanol (3 mL) at room temperature. A solution of potassium hydroxide (3.48 mg, 0.062 mmol) in isopropanol (1 mL) was added, and the mixture was stiired at 45° C. for 1 hour. The mixture was passed through silica gel and washed with ethylacetate. The filtrate was concentrated under reduced pressure to afford the 8-amino-1,2,3,4-tetrahydro-naphthalen-2-ol chiral enantiomer (33.0 mg, 65% yield).

Workup

  1. washwashed with ethylacetate
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e74f8272bc2b40c3b4cbe70e4f34af57
Source dataset
uspto-grants-2012_01
Patent number
US08088826B2

Reaction notes

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