4-Benzyl-2-methyl-6-(trifluoromethyl)morpholin-3-one → 4-Benzyl-cis-2-methyl-6-(trifluoromethyl)morpholine

Participants

Reaction Conditions

Reaction Steps

Dry LiAlH4 (797 mg, 21 mmol, Aldrich) is suspended in dry, inhibitor free THF (15 ml) and treated with a solution of 4-benzyl-2-methyl-6-(trifluoromethyl)morpholin-3-one (2.73 g, 10 mmol) in dry, inhibitor free THF (15 ml). The mixture is heated to 60° C. with stirring for 30 minutes. The mixture is diluted with MTBE (25 mL) and quenched sequentially with H2O (0.8 mL), 6.0M NaOH (0.8 mL) and H2O (2.4 mL). The white slurry is filtered and the inorganic salts were washed with MTBE (200 mL). The solvent is removed by rotary evaporation and the product is purified in 3 portions on Biotage Flash 40M+ cartridges using a 10 minute linear gradient of 3%-10% MTBE in heptane. The products are combined and dried under high vacuum yielding a colorless oil.

Provenance & Evidence