Oxygen → HCID 86664652, compound

Participants

Reaction Steps

A solution of (3S,4S)-3-allyl-4-benzyloxymethyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (6.76 g, 15.0 mmol) in methanol (150 mL) was bubbled with oxygen for five minutes. After bubbling with ozone for 1.5 hours with stirring under cooling with dry ice-methanol, ozone was removed by bubbling with nitrogen. Dimethyl sulfide (5.64 mL, 76.8 mmol) was added under cooling, and the mixture was stirred for 19 hours. The reaction solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→90:10→80:20→75:25→66:34→50:50) to give 4.58 g of the title compound as a transparent oil.

Provenance & Evidence