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

HRID 1975035Notes

Reaction equation

HRID 1975035 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-27f4dff4da604a05ab4932515d2d704c
Source dataset
uspto-grants-1994_02
Patent number
US05284855

Reaction notes

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