Water → HCID 19013344, compound

HRID 1729036Notes

Reaction equation

HRID 1729036 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]([CH:27]([CH3:29])[CH3:28])=[CH:23][CH:24]=3)[C:19](=O)[N:18]2[CH3:31])=[CH:13][CH:12]=1)([CH3:10])([CH3:9])[CH3:8].O.[OH-].[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]([CH:27]([CH3:28])[CH3:29])=[CH:23][CH:24]=3)[CH2:19][N:18]2[CH3:31])=[CH:15][CH:16]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19013340HCID 19013340, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19013344HCID 19013344, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 30 ml of a suspension containing 0.58 g of lithium aluminum hydride in THF, 20 ml of a solution containing 2.57 g of 3-(4-tert-butylphenyl)-7-isopropyl-2-methyl-1,2,3,4-tetrahydroisoquinoline-1-one in THF was added and the resulting mixture was heated to reflux for 15 hours. After the reaction, 0.58 g of water, 0.58 g of 15% aqueous sodium hydroxide solution and 1.8 g of water were sequentially added in the order mentioned while cooling the mixture in ice and the generated precipitates were removed by filtration. After drying the filtrate over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=9/1 v/v) to obtain 2.30 g of 3-(4-tert-butylphenyl)-7-isopropyl-2-methyl-l,2,3,4-tetrahydroisoquinoline.

Workup

  1. additionwas added
  2. temperaturethe resulting mixture was heated
  3. temperatureto reflux for 15 hours
  4. additionwere sequentially added in the order
  5. temperaturewhile cooling the mixture in ice
  6. customthe generated precipitates
  7. customwere removed by filtration
  8. dry with materialAfter drying the filtrate over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=9/1 v/v)

Sources & evidence

ORD record
ord-8ffa6699560c41daaa9f526a0f5730d5
Source dataset
uspto-grants-1994_07
Patent number
US05330991

Reaction notes

Loading…