1-Formyl-4-oxo-2,4,6,7-tetrahydro-pyrrolo[3,4-c]pyridine-5-carboxylic acid tert-butyl ester → 4-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-1-carbaldehyde

HRID 991790Notes

Reaction equation

HRID 991790 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2=[C:14]([CH:17]=[O:18])[NH:15][CH:16]=[C:10]2[C:9]1=[O:19])=O)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[O:19]=[C:9]1[C:10]2=[CH:16][NH:15][C:14]([CH:17]=[O:18])=[C:11]2[CH2:12][CH2:13][NH:8]1

Participants

4

Reactant 1

HCID 129671421-Formyl-4-oxo-2,4,6,7-tetrahydro-pyrrolo[3,4-c]pyridine-5-carboxylic acid tert-butyl ester

Product 1

HCID 99641894-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-1-carbaldehydeYield 75%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1-formyl-4-oxo-2,4,6,7-tetrahydro-pyrrolo[3,4-c]pyridine-5-carboxylic acid tert-butyl ester (1.2 g, 4.54 mmol) in 50% of trifluoroacetic acid in dichloromethane was stirred at room temperature for 30 minutes. The reaction was concentrated and the residue was recrystallized from dichloromethane to give 400 mg (75%) of 4-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-1-carbaldehyde.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was recrystallized from dichloromethane

Sources & evidence

ORD record
ord-aba42653cf8f4b12a6d9e3a70fd2a8d1
Source dataset
uspto-grants-2002_10
Patent number
US06465507B2

Reaction notes

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