tert-Butyl 5-benzylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate → Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylate

HRID 712418Notes

Reaction equation

HRID 712418 reaction equation
C([N:8]1[CH2:12][CH:11]2[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH:10]2[CH2:9]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH2:13]1[CH:11]2[CH2:12][NH:8][CH2:9][CH:10]2[CH2:15][N:14]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Participants

4

Reactant 1

HCID 4171147tert-Butyl 5-benzylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

Product 1

HCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylateYield 91.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 5-benzylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (2.50 g) in MeOH (100 mL) was added a catalytic amount of Pd(OH)2. The suspension was stirred under H2 overnight and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 7:1 (v/v) DCM/MeOH) to give the compound as oil (1.60 g, 90.00%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was chromatographed with a silica gel column (eluting agent: 7:1 (v/v) DCM/MeOH)

Sources & evidence

ORD record
ord-fb297c0771f7411ab9aa08d90373bbd7
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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