Oxygen → HCID 67490777, compound

Participants

Reaction Steps

A solution of (3S,4R)-3-allyl-4-benzyloxymethyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (8.00 g, 17.8 mmol) in methanol (177 mL) was bubbled with oxygen for 10 minutes. After bubbling with ozone for 30 minutes with stirring under cooling with dry ice-methanol, ozone was removed by bubbling with nitrogen. Sodium borohydride (1.68 g, 44.4 mmol) was added under cooling with ice-acetone, and the mixture was stirred under cooling for 1.5 hours. A saturated ammonium chloride solution (150 mL) was added to the reaction solution, and methanol was evaporated by concentration under reduced pressure. The mixture was extracted with ethyl acetate (200 mL×1, 150 mL×1). The organic layer was washed with brine (300 mL) and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→90:10→66:34→50:50) to give 3.79 g of the title compound as a pale yellow oil.

Provenance & Evidence