tert-butyl 6-methyl-5-oxo-3,3a,4,5-tetrahydrocyclopenta[c]pyrrole-2(1H)-carboxylate → tert-butyl 4-methyl-5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

HRID 877690Notes

Reaction equation

HRID 877690 reaction equation
[CH3:1][C:2]1[C:3](=[O:17])[CH2:4][CH:5]2[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7][C:6]=12.[H][H]>CO.ClCCl.[OH-].[OH-].[Pd+2]>[CH3:1][CH:2]1[CH:6]2[CH:5]([CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]2)[CH2:4][C:3]1=[O:17]

Participants

6

Reactant 2

HCID 15638530tert-butyl 6-methyl-5-oxo-3,3a,4,5-tetrahydrocyclopenta[c]pyrrole-2(1H)-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 68291201tert-butyl 4-methyl-5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylateYield 91%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 6-methyl-5-oxo-3,3a,4,5-tetrahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (11.6 g, 48.9 mmol), 20% palladium hydroxide on carbon (3.43 g) in methanol (30 mL) and dichloromethane (30.0 mL) was stirred under 20 psi hydrogen for 3 h. The mixture was then filtered to remove the solid catalyst. The filtrate was concentrated. Silica gel chromatography, eluting with 5-60% ethyl acetate in hexanes, gave tert-butyl 4-methyl-5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate as a 3 to 1 mixture of endo- and exo-isomers (10.7 g, 91% yield).

Workup

  1. filtrationThe mixture was then filtered
  2. customto remove the solid catalyst
  3. concentrationThe filtrate was concentrated
  4. washSilica gel chromatography, eluting with 5-60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-df9a90d8afc0444d833644017e35672d
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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