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

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.

1. temperaturewas heated with 72° C. oil bath overnight
2. temperaturewas cooled down to 0° C.
3. customquenched by sequential addition of H2O (0.47 mL), 3M aqueous solutionueous NaOH (0.47 mL) and H2O (1.4 mL)
4. additionthe quenched residue was diluted with Et2O (30 mL)
5. stirringstirred for 10 min
6. customthe ethereal solution was separated by filtration
7. concentrationThe filtrate was concentrated
8. customfurther dried under vacuum

ORD record

ord-4d9fb5b0a78e48f7b6dcbaa8e988c92f

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242996B2