Ozone → tert-Butyl alpha-(2-Hydroxyethyl)-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate

Participants

Reaction Steps

Ozone is bubbled through a solution of tert-butyl 3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-α-(propen-2-yl)-3-pyrrolidineacetate (555 mg, 1.39 mmol) and EtOH (12 mL) at -78° C. for 5 minutes. Nitrogen is then bubbled through the solution for 5 minutes. Sodium borohydride (79 mg, 2.1 mmol) is added and the mixture is allowed to warm slowly and to stir at room temperature overnight. The mixture is concentrated to near dryness, and aqueous workup (EtOAc, MgSO4) to give 511 mg (91%) of the title compound as a colorless oil.

Provenance & Evidence