Acetone → HCID 15157378, compound

HRID 2051436Notes

Reaction equation

HRID 2051436 reaction equation
[NH2:1][CH:2]1[CH:14]2[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13]2)[C:8]2[C:3]1=[C:4]([OH:17])[C:5]([CH3:16])=[CH:6][C:7]=2[CH3:15].C(=O)([O-])[O-].[K+].[K+].CC(C)=O.Cl[CH2:29][CH2:30][CH2:31][C:32](Cl)=[O:33]>O>[OH:17][C:4]1[C:5]([CH3:16])=[CH:6][C:7]([CH3:15])=[C:8]2[C:3]=1[CH:2]([N:1]1[CH2:29][CH2:30][CH2:31][C:32]1=[O:33])[CH:14]1[CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 783704-Chlorobutyryl chlorideHCID 15157235HCID 15157235, compound

Product 1

HCID 15157378HCID 15157378, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.0 Grams of 9-amino-8-hydroxy-5,7-dimethyl-1,2,3,4,4a,9a-hexahydrofluorene and 2.5 g of potassium carbonate were added to a mixture of 50 ml of acetone and 20 ml of water and thereto was added dropwise 2.5 ml of γ-chlorobutyryl chloride under ice-cooling and stirring. After stirring for 2 hours, the reaction mixture was concentrated and to the residue was added water and extraction was effected with chloroform. The choroform layer was dried with magnesium sulfate and concentrated. Then, the residue was dissolved in 30 ml of DMF and to the solution was added 2.0 g of sodium hydride (60% oiliness), followed by stirring to generate a gas with generation of heat. Then, the reaction mixture was stirred at room temperature overnight and thereafter concentrated. To the residue was added water and extraction was effected with chloroform. The chloroform layer was dried with magnesium sulfate and concentrated. To the residue was added ethyl acetate and the produced precipitate was collected by filtration and recrystallized from hydrous ethanol to obtain 2.0 g of 8-hydroxy-5,7-dimethyl-9-(2-oxo-1-pyrrolidinyl)-1,2,3,4,4a,9a-hexahydrofluorene having a melting point of 240°-213° C. (decomposed) and of light brown powdery crystal.

Workup

  1. temperaturecooling
  2. stirringAfter stirring for 2 hours
  3. concentrationthe reaction mixture was concentrated and to the residue
  4. additionwas added
  5. extractionwater and extraction
  6. dry with materialThe choroform layer was dried with magnesium sulfate
  7. concentrationconcentrated
  8. dissolutionThen, the residue was dissolved in 30 ml of DMF and to the solution
  9. additionwas added 2.0 g of sodium hydride (60% oiliness)
  10. stirringby stirring
  11. temperatureof heat
  12. stirringThen, the reaction mixture was stirred at room temperature overnight
  13. concentrationconcentrated
  14. additionTo the residue was added
  15. extractionwater and extraction
  16. dry with materialThe chloroform layer was dried with magnesium sulfate
  17. concentrationconcentrated
  18. additionTo the residue was added ethyl acetate
  19. filtrationthe produced precipitate was collected by filtration
  20. customrecrystallized from hydrous ethanol

Sources & evidence

ORD record
ord-ad8eab0cacf04ce0a059d1a12fb171ab
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

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