Acetone → HCID 14771965, compound

Participants

Reaction Steps

Phenylmethyl 2,5-dihydro-1H-pyrrole-1-carboxylate (commercially-available) (5.07 g, 25 mmol) was dissolved in a mixture of acetone (25 mL) and water (10 mL). NMO (5.9 g, 50 mmol) was added followed by catalytic OsO4. The reaction was stirred for 19 hours and then quenched by the addition of an aqueous solution of Na2S2O3. A standard work-up followed by silica gel chromatography (3:1 Hexane:ethyl acetate to pure ethyl acetate to 9:1 DCM: MeOH) yielded phenylmethyl (cis)-3,4-dihydroxy-1-pyrrolidinecarboxylate (0.872 g, 15%) as a clear oil. LCMS: (M+H)+: 237.9.

Provenance & Evidence