Sodium Sulfate → HCID 15157379, compound

HRID 2051437Notes

Reaction equation

HRID 2051437 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[OH:7][C:8]1[C:9]([CH3:28])=[CH:10][C:11]([CH3:27])=[C:12]2[C:20]=1[CH:19]([N:21]1[CH2:25][CH2:24][CH2:23][C:22]1=O)[CH:18]1[CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17]1.[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.C(OCC)(=O)C>[OH:7][C:8]1[C:9]([CH3:28])=[CH:10][C:11]([CH3:27])=[C:12]2[C:20]=1[CH:19]([N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)[CH:18]1[CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

7

Reactant 4

HCID 24436Sodium SulfateHCID 166653HydrideHCID 15157378HCID 15157378, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15157379HCID 15157379, compoundYield 69.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.34 Gram of aluminum lithium hydride was suspended in 30 ml of THF and to the suspension was gradually added dropwise 1.6 g of 8-hydroxy-5,7-dimethyl 9-(2-oxo-1-pyrrolidinyl)-1,2,3,4,4a,9a-hexahydrofluorene. This suspension was refluxed with heating for 5 hours and then ice-cooled and excess hydride was decomposed with ethyl acetate. To the reaction mixture was added 1.5 ml of saturated aqueous sodium sulfate solution, followed by stirring at room temperature for 1 hour and then filtration to remove the precipitate. The filtrate was concentrated and to the residue was added ethyl acetate and insoluble matter was removed by filtration. The filtrate was again concentrated and the residue was recrystallized from hydrous ethanol to obtain 1.06 g of 8-hydroxy-5,7-dimethyl-9-(1-pyrrolidinyl)-1,2,3,4,4a,9a-hexahydrofluorene having a melting point of 96°-97° C. and of colorless prism-like crystal.

Workup

  1. temperatureThis suspension was refluxed
  2. temperaturewith heating for 5 hours
  3. temperatureice-cooled
  4. filtrationfiltration
  5. customto remove the precipitate
  6. concentrationThe filtrate was concentrated and to the residue
  7. additionwas added ethyl acetate and insoluble matter
  8. customwas removed by filtration
  9. concentrationThe filtrate was again concentrated
  10. customthe residue was recrystallized from hydrous ethanol

Sources & evidence

ORD record
ord-8534d8dffca0476c9dcaa11811ebe3f8
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

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