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

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Reaction Steps

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.

Provenance & Evidence