Ethyl 1-benzylhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate → Ethyl hexahydropyrrolo[3,4-B]pyrrole-5(1H)-carboxylate

HRID 1590160Notes

Reaction equation

HRID 1590160 reaction equation
C([N:8]1[CH2:15][CH2:14][CH:13]2[CH:9]1[CH2:10][N:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12]2)C1C=CC=CC=1>C(O)C.[Pd]>[CH:9]12[CH2:10][N:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH:13]1[CH2:14][CH2:15][NH:8]2

Participants

4

Reactant 1

HCID 11086974Ethyl 1-benzylhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

Product 1

HCID 19100952Ethyl hexahydropyrrolo[3,4-B]pyrrole-5(1H)-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

21.2 g (77.3 mmol) of ethyl 2-benzyl-2,7-diazabicyclo[3.3.0]octane-7-carboxylate (Example Ae) in 400 ml of ethanol are hydrogenated on 3 g of palladium/active carbon (10% Pd) at 100° C. and 100 bar. The catalyst is filtered off, the filtrate is concentrated, and the residue is distilled.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated
  3. distillationthe residue is distilled

Sources & evidence

ORD record
ord-28273d2cd9944dcaa351f75aecb76743
Source dataset
uspto-grants-1993_04
Patent number
US05202337

Reaction notes

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