Water → HCID 19013343, compound

HRID 1729035Notes

Reaction equation

HRID 1729035 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][C:22]([CH3:27])=[CH:23][CH:24]=3)[C:19](=O)[N:18]2[CH3:29])=[CH:13][CH:12]=1)([CH3:10])([CH3:9])[CH3:8].O.[Na]>C1COCC1>[C:7]([C:11]1[CH:12]=[CH:13][C:14]([CH:17]2[CH2:26][C:25]3[C:20](=[CH:21][C:22]([CH3:27])=[CH:23][CH:24]=3)[CH2:19][N:18]2[CH3:29])=[CH:15][CH:16]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 962Water2×HCID 5360545SodiumHCID 19013338HCID 19013338, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19013343HCID 19013343, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 70 ml of a suspension containing 1.28 g of lithium aluminum hydride in THF, 30 ml of a solution containing 4.93 g of 3-(4-tert-butylphenyl)-2,7-dimethyl-1,2,3,4-tetrahydroisoquinoline-1-one in THF was added and the resulting mixture was heated to reflux for 14 hours.After the reaction, 1.28 g of water, 1.28 g of 15% aqueous sodium hydroxidesolution and 3.84 g of water were sequentially added in the order mentionedwhile cooling the mixture in ice and the generated precipitates were removed by filtration. The filtrate was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residuewas purified by column chromatography on silica gel (hexane/ethyl acetate=9/1 v/v) to obtain 4.22 g of 3- (4-tert-butylphenyl ) -2,7-dimethyl-1.2,3,4-tetrahydroisoquinoline.

Workup

  1. additionwas added
  2. temperaturethe resulting mixture was heated
  3. temperatureto reflux for 14 hours
  4. additionwere sequentially added in the order mentionedwhile
  5. temperaturecooling the mixture in ice
  6. customthe generated precipitates
  7. customwere removed by filtration
  8. dry with materialThe filtrate was dried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residuewas purified by column chromatography on silica gel (hexane/ethyl acetate=9/1 v/v)

Sources & evidence

ORD record
ord-860d1747eebd47b0856051bab3d70c20
Source dataset
uspto-grants-1994_07
Patent number
US05330991

Reaction notes

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