Methyl morpholine oxide → Benzyl 3,3-dimethyl-4-oxopyrrolidine-1-carboxylate

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Reaction Steps

To a solution of phenylmethyl (4R)-4-hydroxy-3,3-dimethyl-1-pyrrolidinecarboxylate (1.4088 g, 5.651 mmol) in MeCN (50 mL) was added N-methylmorpholine-N-oxide (0.861 g, 7.350 mmol) and tetra-N-propylammonium perruthenate (0.099 g, 0.282 mmol). The solution was stirred for 90 min, concentrated in vacuo, and purified directly by silica gel chromatography (20% EtOAc in hexanes) to give phenylmethyl 3,3-dimethyl-4-oxo-1-pyrrolidinecarboxylate (1.1321 g, 79%) as a colorless oil. LCMS: (M+Na)+: 270.4.

Provenance & Evidence