5-Benzylhexahydropyrrolo[3,4-c]pyrrole-1-one → Octahydropyrrolo[3,4-c]pyrrol-1-one

HRID 490473Notes

Reaction equation

HRID 490473 reaction equation
C([N:8]1[CH2:12][CH:11]2[CH2:13][NH:14][C:15](=[O:16])[CH:10]2[CH2:9]1)C1C=CC=CC=1>C(O)C.C(#N)C.[Pd]>[C:15]1(=[O:16])[CH:10]2[CH2:9][NH:8][CH2:12][CH:11]2[CH2:13][NH:14]1

Participants

5

Reactant 1

HCID 671476375-Benzylhexahydropyrrolo[3,4-c]pyrrole-1-one

Product 1

HCID 22562203Octahydropyrrolo[3,4-c]pyrrol-1-one

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 5-benzylhexahydropyrrolo[3,4-c]pyrrole-1-one, (7.2 g; 33 mmol) in absolute ethanol (100 ml) is placed in a 250 ml autoclave and palladium-on-charcoal at 5% (1.5 g) is then added. After having purged with nitrogen, the autoclave is placed under 5-6 bar of hydrogen at 70° C. for 16 hours. After returning to 20° C., the catalyst is filtered off and the filtrate is evaporated under reduced pressure. The compound obtained is taken up in acetonitrile (15 ml) at reflux, filtered, under hot conditions, through paper and then crystallized. After crystallization, the solid obtained is filtered off, washed with acetonitrile (3 ml) and then with diethyl ether (20 ml) and, finally, dried under reduced pressure at constant weight. Hexahydropyrrolo[3,4-c]pyrrole-1-one, (1.3 g; 31%) is isolated, the characteristics of which are as follows:

Workup

  1. additionis then added
  2. customAfter having purged with nitrogen
  3. customAfter returning to 20° C.
  4. filtrationthe catalyst is filtered off
  5. customthe filtrate is evaporated under reduced pressure
  6. customThe compound obtained
  7. temperatureat reflux
  8. filtrationfiltered, under hot conditions, through paper
  9. customcrystallized
  10. customAfter crystallization
  11. customthe solid obtained
  12. filtrationis filtered off
  13. washwashed with acetonitrile (3 ml)
  14. dry with materialwith diethyl ether (20 ml) and, finally, dried under reduced pressure at constant weight

Sources & evidence

ORD record
ord-60123edfec4d4114bb5e194a555d0336
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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