[CH2:1]([CH:3]1[CH2:6][NH:5][C:4]1=[O:7])[CH3:2].[C:8]([O-:11])(=[O:10])[CH3:9].[Na+].C(O)(=O)C.C(OO)(=O)C>C(OCC)(=O)C.O.O.O.[Os](Cl)(Cl)Cl.O>[C:8]([O:11][CH:6]1[NH:5][C:4](=[O:7])[CH:3]1[CH2:1][CH3:2])(=[O:10])[CH3:9]
To a solution prepared by mixing 500 mg (5 mmole) of 3-ethylazetidin-2-one, 415 mg (5 mmole) of anhydrous sodium acetate, 5 ml of acetic acid, and 30 mg (abut 2 mole % based on the amount of 3-ethylazetidin-2-one) of osmium trichloride trihydrate was added dropwise, with stirring , 2.8 g (11 mmole) of a 30% peracetic acid solution in ethyl acetate at room temperature over a period of 2 hours or more. The reaction mixture was further stirred at room temperature for 4 hours, subsequently poured into 80 ml of water, and then extracted thrice with 100 ml of hexane. The extract was dried over anhydrous magnesium sulfate, and the solvent was removed by evaporation under reduced pressure. The residue was separated and purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1 by volume). Thus, 780 mg of 4-acetoxy-3-ethylazetidin-2-one was obtained. The percent yield was 78%.
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