Sodium Hydroxide → HCID 15239361, compound

HRID 1609489Notes

Reaction equation

HRID 1609489 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19](=O)[N:18]2[CH3:28])=[CH:13][CH:12]=1)([CH3:10])([CH3:9])[CH3:8].[OH-].[Na+]>C1COCC1.O>[C:7]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][N:18]2[CH3:28])=[CH:13][CH:12]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 15239360HCID 15239360, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15239361HCID 15239361, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 20 ml of THF in which 0.83 g of lithium aluminum hydride is suspended, 20 ml of a solution containing 0.32 g of 3-(4-t-butylphenyl)-2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinoline in THF was added and the mixture was heated to reflux for 4 hours. After the reaction, 10 ml of 10% aqueous sodium hydroxide solution was gradually added to the resulting mixture cooled in iced water and the generated precipitates were removed by filtration through Celite. After concentrating the filtrate, the aqueous layer was extracted with ethyl acetate (40 ml×2). After washing the combined organic layers with brine (50 ml×1), the organic layers were dried over anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by silica gel column chromatography [hexane/ethyl acetate (6/1)] to obtain 0.24 g of 3-(4-t-butylphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 4 hours
  4. additionwas gradually added to the resulting mixture
  5. customthe generated precipitates
  6. customwere removed by filtration through Celite
  7. concentrationAfter concentrating the filtrate
  8. extractionthe aqueous layer was extracted with ethyl acetate (40 ml×2)
  9. washAfter washing the combined organic layers with brine (50 ml×1)
  10. dry with materialthe organic layers were dried over anhydrous magnesium sulfate
  11. customAfter evaporating the solvent under reduced pressure
  12. customthe residue was purified by silica gel column chromatography [hexane/ethyl acetate (6/1)]

Sources & evidence

ORD record
ord-092ddaecf3064a48a2540931f01a9b34
Source dataset
uspto-grants-1995_03
Patent number
US05401752

Reaction notes

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