Dimethylformamide dimethyl acetal → tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 4-oxopiperidine-1-carboxylate (10 g, 50.25 mmol) in DMF (500 mL) at room temperature was added DMF-DMA (14.9 g, 125.62 mmol). The reaction mixture was heated at 100° C. for 48 hours. After completion of reaction the solvent was removed under reduced pressure and the resulting residue dissolved in EtOAc (300 mL) and extracted with water (2×200 mL). This organic layer was dried using sodium sulfate and concentrated under reduced pressure to give crude desired product, tert-butyl 3-((dimethylamino)methylene)-4-oxopiperidine-1-carboxylate (10.2 g, 79%), which was used in the next step without any further purification. LCMS [M+H]:255.

Provenance & Evidence