(5S)-5-Phenyl-3-morpholinone → (3S)-3-Phenylmorpholine

Participants

Reaction Steps

To a LiAlH4/THF slurry (0.47 g/2 mL) was added dropwise (S)-5-phenylmorpholin-3-one in THF solution (481 mg in 6 mL) at room temperature over 5 min. The resulting mixture was stirred at room temperature thereafter for 1 hour, then was heated with 72° C. oil bath overnight, then was cooled down to 0° C., quenched by sequential addition of H2O (0.47 mL), 3M aqueous solutionueous NaOH (0.47 mL) and H2O (1.4 mL), and the quenched residue was diluted with Et2O (30 mL), stirred for 10 min and the ethereal solution was separated by filtration. The filtrate was concentrated, further dried under vacuum and (S)-3-phenylmorpholine (424 mg, 96% yield) was obtained as colorless solid. LCMS (m/z): 164.2 (MH+), 0.33 min.

Provenance & Evidence