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

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl (2S,3S)-3-hydroxy-2-methylpyrrolidine-1-carboxylate (20.5 g) in acetonitrile (150 mL) were added powdery molecular sieves 4 A (25 g) and 4-methylmorpholine-N-oxide (20.4 g). After cooling 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. Insoluble materials were 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, 89%).

Provenance & Evidence