Aluminium lithium hydride → HCID 66873902, compound

Participants

Reaction Conditions

Reaction Steps

To an ice-cold 1.0M solution of LiAlH4 in THF (4.10 mL, 4.10 mmol) was added a solution of (4aS,8aS)-4-(2,4-dimethoxybenzyl)octahydroquinoxalin-2(1H)-one (500 mg, 1.64 mmol) in THF (10 mL). The mixture was heated at reflux for 8 h. The reaction was cooled to 0° C. and carefully quenched with EtOAc (50 mL) and 1 N NaOH solution (20 mL). The mixture stirred for 30 min and the layers were separated. The organic layer was washed with brine (20 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. Purification of the residue by column chromatography (silica gel, 0% to 60% 90:9:1 CH2Cl2/CH3OH/NH4OH in CH2Cl2) afforded (4aS,8aS)-1-(2,4-dimethoxybenzyl)decahydroquinoxaline (120.1 mg, 25.4%). 1H NMR and MS consistent.

Provenance & Evidence