Pyrrolidine → HCID 86732730, compound

Participants

Reaction Steps

A solution of pyrrolidine (0.295 mL, 3.57 mmol) and 3-((4-methoxybenzyl)oxy)-1-methyl-4-oxo-1,4-dihydroquinoline-6-carbaldehyde (1.05 g, 3.25 mmol) in 1,2-dichloroethane (DCE) (50 mL) and 1 drop of acetic acid was treated with sodium triacetoxyborohydride (1.032 g, 4.87 mmol). The reaction mixture was stirred for 1.5 h, and was then concentrated under vacuum. The residue was taken in water (50 mL), and extracted with dichloromethane (2×50 mL). The organic layers were combined, washed with brine (50 mL), dried over sodium sulfate, and concentrated. The crude product was purified twice by automatic silica gel column chromatography (Combiflash RF), eluting with a mixture of [dichloromethane/methanol/ammonium hydroxide (80:20:2)]/dichlormethane (0-40%) to afford pure 3-((4-methoxybenzyl)oxy)-1-methyl-6-(pyrrolidin-1-ylmethyl)quinolin-4(1H)-one (1 g, 2.64 mmol, 81% yield) as a light yellow solid. LCMS: (M+H)+: 379.5.

Provenance & Evidence