Aluminium lithium hydride → (2S,6S)-4-Benzyl-2,6-dimethylmorpholine

Participants

Reaction Conditions

Reaction Steps

(2S,6S)-4-benzoyl-2,6-dimethylmorpholine (759 mg, 3.46 mmol) is dissolved in anhydrous THF (40 mL) and treated with LiAlH4 (1.0 M in THF, 6.9 mL, Aldrich). The mixture is stirred with heating at 55° C. for 18 hours. An additional equivalent of LiAlH4 is added and the mixture is stirred with heating at 55° C. for an additional 6 hours. The reaction is quenched by adding water (0.4 mL) followed by 6.0 M NaOH (0.4 mL) followed by water (1.2 mL). The white slurry is diluted with Et2O and filtered. The inorganic salts are washed with and additional portion of Et2O and the combined ethereal washes are dried over Na2SO4. The product is purified on a Biotage Flash 40M+ using a 15% Et2O in pentane as eluent. The product containing fractions are pooled and the solvent is removed by rotary evaporation. The product is dried under vacuum yielding a colorless oil.

Provenance & Evidence