(5S)-4-[(4-Methoxyphenyl)methyl]-5-methylmorpholin-3-one → HCID 59525840, compound

Participants

Reaction Conditions

Reaction Steps

Into a 5000 mL 4-necked, round bottomed flask purged and maintained with an inert atmosphere of nitrogen was placed a suspension of lithium aluminum hydride (60.04 g, 1.58 mol) in THF (2000 mL), followed by the dropwise addition of a solution of (S)-4-(4-methoxybenzyl)-5-methylmorpholin-3-one (186 g, 790.48 mmol) in THF (300 mL). The resulting solution was heated to reflux for 1 hour. The reaction mixture was cooled to 0° C., quenched by adding 500 mL of ethyl acetate and then 500 mL of water, the resulting solution was extracted three times with 2000 mL of ethyl acetate. The combined organic layer was dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by flash chromatography (silica, 1:30 ethyl acetate/petroleum ether) to afford the title compound as a yellow oil.

Provenance & Evidence