Methyl morpholine oxide → benzyl (2S)-2-methyl-3-oxopyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution (150 mL) of benzyl (2S,3S)-3-hydroxy-2-methylpyrrolidine-1-carboxylate (20.5 g) in acetonitrile were added molecular sieves 4A powder (25 g) and 4-methylmorpholine-N-oxide (20.4 g), and the mixture was cooled to 0° C. tetra-n-Propylammonium perruthenate (3.0 g) was added, and the mixture was stirred at 0° C. for 1 hr and at room temperature for 18 hr. The reaction mixture was concentrated under reduced pressure, and the residue was suspended in ethyl acetate. The insoluble material was filtered through Hyflo Super-Cel. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1→2/1) to give the title compound as a colorless oil (yield: 18.0 g, yield: 89%).

Provenance & Evidence