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

HRID 2194938Notes

Reaction equation

HRID 2194938 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(OCC)(=O)C.CCCCCC>CC(O)C.[Ru](Cl)Cl.C1C=CC=CC=1.[Ru]>[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

8

Reactant 4

HCID 14797Potassium HydroxideHCID 9866743(1S,2R)-(-)-1-Amino-2-indanolHCID 21226206Ethyl acetate hexaneHCID 230669938-Amino-3,4-dihydro-1H-naphthalen-2-one

Product 1

HCID 57936087(2R)-8-Amino-1,2,3,4-tetrahydro-2-naphthalenolYield 64.3%

Reagents, catalysts & solvents 3

HCID 23950RutheniumCatalystHCID 11096978HCID 11096978, compoundCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

Benzene ruthenium(II)chloride dimmer (0.2 g, 0.0004 mol, 0.02 eq), (1S,2R)-(−)-cis-1-Amino-2-indanol (0.24 g, 0.0016 mol, 0.08 eq) were taken in nitrogen bubbled IPA (50 ml). This solution was heated at 80° C. for 20 min and cooled back to RT. 8-amino-3,4-dihydronaphthalen-2(1H)-one (3.3 g, 0.02 mol) was taken in nitrogen bubbled IPA (98 ml), a solution of KOH (0.23 g, 0.004 mol, 0.2 eq) in IPA (50 ml) and the earlier prepared ruthenium solution were added drop wise simultaneously at RT. The overall reaction mixture was heated to 45° C. and stirred for 30 min at the same temperature. Progress of the reaction was monitored by TLC (50% ethyl acetate/hexane, Rf˜0.2). On completion of the reaction, cooled the reaction contents to rt, filtered on a silica gel bed and the bed was washed with ethyl acetate (4×30 ml). Filtrate was concentrated under reduced pressure, residue was taken in DCM (75 ml) and treated with charcoal. Filtered the contents over a silica gel bed and the bed washed with DCM (4×30 ml). DCM was distilled off completely and the crude obtained was purified by column chromatography (silica gel, 20% ethyl acetate/hexane) to yield the titled product as a brown colored solid (2.1 g, 63% yield, mp 58-87° C.).

Workup

  1. custombubbled IPA (50 ml)
  2. temperaturecooled back to RT
  3. custombubbled IPA (98 ml)
  4. additionwere added drop wise simultaneously at RT
  5. temperatureThe overall reaction mixture was heated to 45° C.
  6. customOn completion of the reaction
  7. temperaturecooled
  8. customthe reaction contents to rt
  9. filtrationfiltered on a silica gel bed
  10. washthe bed was washed with ethyl acetate (4×30 ml)
  11. concentrationFiltrate was concentrated under reduced pressure, residue
  12. additiontreated with charcoal
  13. filtrationFiltered the contents over a silica gel bed
  14. washthe bed washed with DCM (4×30 ml)
  15. distillationDCM was distilled off completely
  16. customthe crude obtained
  17. customwas purified by column chromatography (silica gel, 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2ca404c6379d4a98a9ac8968bdfd7643
Source dataset
uspto-grants-2012_12
Patent number
US08334315B2

Reaction notes

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