N#N.[F:3][C:4]([F:18])([F:17])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])=[CH:7][CH:6]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C1(S(N2C(C3C=CC=CC=3)O2)(=O)=[O:36])C=CC=CC=1>O1CCCC1>[OH:36][CH:13]1[CH2:14][CH2:15][N:11]([C:8]2[CH:7]=[CH:6][C:5]([C:4]([F:3])([F:17])[F:18])=[CH:10][CH:9]=2)[C:12]1=[O:16]
(Referring to Scheme 1) To a 100 mL round-bottomed flask equipped with septum and N2 inlet were added 600 mg (2.62 mmol) 1-(4-trifluoromethyl-phenyl)-pyrrolidin-2-one and 25 mL dry tetrahydrofuran. The solution was cooled to −78° C., and 5.24 mL (5.24 mmol) of a 1 M solution of lithium hexamethyldisilazide in tetrahydrofuran was added, and the reaction was stirred at −78° C. for 45 minutes. Then a solution of 856 mg (3.27 mmol) of N-(benzenesulfonyl)phenyloxaziridine in 5 mL dry tetrahydrofuran was added, and the reaction allowed to warm to room temperature and stirred overnight. The reaction was quenched with aqueous ammonium chloride solution and diluted with ethyl acetate, and the layers were separated. The aqueous phase was extracted three times with ethyl acetate, and the combined organic phase dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel with hexane/ethyl acetate to afford 241 mg (38%) of a while solid.
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