Pyrrolidine → HCID 178442476, compound

HRID 1737154Notes

Reaction equation

HRID 1737154 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[C:11](=[O:12])[C:10]([OH:13])=[CH:9][C:7](=[O:8])[C:5]=2[CH:6]=1.[CH3:14][C:15]([CH3:20])([CH3:19])[CH2:16][CH:17]=O.N1CCCC1>C1COCC1>[CH3:14][C:15]([CH3:20])([CH3:19])[CH:16]=[CH:17][C:9]1[C:7](=[O:8])[C:5]2[C:4]([C:11](=[O:12])[C:10]=1[OH:13])=[CH:3][CH:2]=[CH:1][CH:6]=2

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 763353,3-DimethylbutanalHCID 178516607HCID 178516607, compound

Product 1

HCID 178442476HCID 178442476, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lawsone (2-hydroxynaphthalene-1,4-dione) (1.4 g) and 3,3-dimethyl-butanal (1.0 g) were dissolved in 20 ml THF at room temperature and 795 μl pyrrolidine added before stirring the reaction for a further 20 minutes. The solvent was removed under vacuum and the residue dissolved in benzene (40 ml) before addition of p-toluenesulphonic acid (2.3 g). The mixture was refluxed for 1 hour, cooled then diluted with ether before the organic phase was washed with sodium bicarbonate solution, followed by one wash with dilute HCl and one wash with water followed by drying under vacuum. The product was purified by chromatograpy using 10% EtOAc/petroleum ether eluant and then crystallised from methanol to yield 260 mg; m.p. 126-128° C.

Workup

  1. customthe reaction for a further 20 minutes
  2. customThe solvent was removed under vacuum
  3. dissolutionthe residue dissolved in benzene (40 ml) before addition of p-toluenesulphonic acid (2.3 g)
  4. temperatureThe mixture was refluxed for 1 hour
  5. temperaturecooled
  6. additionthen diluted with ether before the organic phase
  7. washwas washed with sodium bicarbonate solution
  8. washwash with dilute HCl and one
  9. washwash with water
  10. customby drying under vacuum
  11. customThe product was purified by chromatograpy
  12. customcrystallised from methanol
  13. customto yield 260 mg

Sources & evidence

ORD record
ord-7f58d444b0104c8cba8784e2d0f4b791
Source dataset
uspto-grants-1999_10
Patent number
US05962002

Reaction notes

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