2,4-Dimethoxybenzaldehyde → HCID 66874912, compound

Participants

Reaction Steps

A mixture of (4aS,8aS)-octahydroquinoxalin-2(1H)-one (8.82 g, 57.19 mmol), 2,4-dimethoxybenzaldehyde (9.50 g, 57.19 mmol), and sodium triacetoxyborohydride (36.31 g, 171.57 mmol) in 1% HOAc in CH2Cl2 (250 mL) was stirred at room temperature for 16 h. The mixture was neutralized with saturated aqueous NaHCO3 solution (200 mL). The organic layer was separated and washed with H2O (100 mL), brine (100 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. Purification of the residue by column chromatography (silica gel, 0% to 100% 90:9:1 CH2Cl2/CH3OH/NH4OH in CH2Cl2) afforded (4aS,8aS)-4-(2,4-dimethoxybenzyl)octahydroquinoxalin-2(1H)-one (1.10 g, 11.1% over two steps). 1H NMR and MS consistent.

Provenance & Evidence