5-Benzyl-octahydropyrrolo(3,4-c)pyrrole-1,3-dione → Perhydropyrrolo(3,4-c)pyrrole-1,3-dione

HRID 2426866Notes

Reaction equation

HRID 2426866 reaction equation
C([N:8]1[CH2:12][CH:11]2[C:13](=[O:17])[NH:14][C:15](=[O:16])[CH:10]2[CH2:9]1)C1C=CC=CC=1>C(O)C.[Pd]>[C:13]1(=[O:17])[CH:11]2[CH2:12][NH:8][CH2:9][CH:10]2[C:15](=[O:16])[NH:14]1

Participants

4

Reactant 1

HCID 45649025-Benzyl-octahydropyrrolo(3,4-c)pyrrole-1,3-dione

Product 1

HCID 21476587Perhydropyrrolo(3,4-c)pyrrole-1,3-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution 5-benzyl-tetrahydropyrrolo[3,4-c]pyrrole-1,3-dione, (11.5 g; 49.9 mmol) in ethanol (200 ml) is placed in a ml autoclave and palladium-on-charcoal (5%; 2 g; 0.9 mmol) is then added. After having purged the reactor with nitrogen, the autoclave is placed under 58 bars of hydrogen at 70° C. for 16 hours. After returning to 20° C., filtration and washing of the catalyst, evaporation is carried out under reduced pressure and the solid obtained is then recrystallized from methanol (100 ml) and drying is carried out under reduced pressure at constant weight. Perhydropyrrolo[3,4-c]pyrrole-1,3-dione, (3.6 g) is isolated, the characteristics of which are as follows:

Workup

  1. additionis then added
  2. customAfter having purged the reactor with nitrogen
  3. customAfter returning to 20° C.
  4. filtrationfiltration
  5. washwashing of the catalyst, evaporation
  6. customthe solid obtained
  7. customis then recrystallized from methanol (100 ml)
  8. customdrying

Sources & evidence

ORD record
ord-f93aa7a6574345048f6373726ffc03c4
Source dataset
uspto-grants-2011_06
Patent number
US07968566B2

Reaction notes

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