Formaldehyde → HCID 68338070, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of (E)-ethyl 3-(2-oxo-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4′-piperidine]-6-yl)acrylate (99.8 mg, 0.316 mmol) in 1,2-dichloroethane (5 mL) were added sodium triacetoxyborohydride (139 mg, 0.656 mmol) and paraformaldehyde (21 mg, 0.699 mmol). The reaction mixture was heated to 70° C. for 5 h. After cooling to room temperature, the reaction mixture was partitioned between DCM (25 mL) and water (25 mL). The aqueous layer was separated and extracted with DCM (2×20 mL). The combined organic phases were washed with saturated NaHCO3 (3×25 mL) and brine (25 mL), dried over sodium sulfate and concentrated. The crude product was used directly in the next step.

Provenance & Evidence