Dimethylformamide → 1-Formyl-4-oxo-2,4,6,7-tetrahydro-pyrrolo[3,4-c]pyridine-5-carboxylic acid tert-butyl ester
Reaction equation
O=P(Cl)(Cl)Cl.[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][C:16]2=[CH:19][NH:20][CH:21]=[C:15]2[C:14]1=[O:22])=[O:12])([CH3:9])([CH3:8])[CH3:7].CN([CH:26]=[O:27])C>>[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][C:16]2=[C:19]([CH:26]=[O:27])[NH:20][CH:21]=[C:15]2[C:14]1=[O:22])=[O:12])([CH3:9])([CH3:7])[CH3:8]Participants
Procedure
POCl3 (0.646 mL, 6.93 mmol) was added dropwise to the ice-cooled DMF (1.5 mL, 18.9 mmol). After stirring at room temperature for 30 minutes, the mixture was re-cooled to −5° C. and to it was added a solution of the above 4-oxo-2,4,6,7-tetrahydro-pyrrolo[3,4-c]pyridine-5-carboxylic acid tert-butyl ester (1.5 g, 6.3 mmol) in DMF (3 mL). The mixture was stirred at room temperature for 6 hours. The reaction mixture was quenched with ice cubes followed by the addition of 10 N potassium hydroxide, adjusting pH to 11-12. After stirring for 30 minutes, the mixture was extracted with ethyl acetate. The combined extracts were washed with brine, dried, and concentrated to give 1.2 g of 1-formyl-4-oxo-2,4,6,7-tetrahydro-pyrrolo[3,4-c]pyridine-5-carboxylic acid tert-butyl ester.
Workup
- temperaturethe mixture was re-cooled to −5° C. and to it
- stirringThe mixture was stirred at room temperature for 6 hours
- customThe reaction mixture was quenched with ice cubes
- additionfollowed by the addition of 10 N potassium hydroxide
- stirringAfter stirring for 30 minutes
- extractionthe mixture was extracted with ethyl acetate
- washThe combined extracts were washed with brine
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-bb02a52e173a48db9c4982794434ca48
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06465507B2
Reaction notes
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