Nitrogen → HCID 19705520, compound

Participants

Reaction Steps

Ozone is bubbled through a cold (-78° C.) solution of tert-butyl 3-(2-methylpropyl)-2-oxo-1-(phenylmethyl)-α-(propen-2-yl)-3-pyrrolidineacetate (1.32 g, 3.42 mmol) in EtOH (30 mL). After purging the solution with N2, sodium borohydride (195 mg, 5.14 mmol) is added in one portion (at -78° C.). The solution is allowed to slowly warm to room temperatuare under N2 overnight. The reaction mixture is concentrated to a white solid, diluted with H2O (10 mL) and extracted with EtOAc (3×25 mL). The organic extracts are combined, washed with brine (25 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to yield 1.37 g of a clear, colorless oil. The oil is purified by silica gel chromatography (50 g SG, 20% EtOAc/hexane) to give 850 mg (64%) of the title compound as a clear, colorless oil, which is a single diastereomer.

Provenance & Evidence