[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=[O:14])[C:9]2=[O:16])=[CH:4][CH:3]=1.CO.[CH2:19]1COCC1.[N+](=C[Si](C)(C)C)=[N-]>CCOCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][CH2:11][CH:10]([C:13]([O:15][CH3:19])=[O:14])[C:9]2=[O:16])=[CH:6][CH:7]=1
To a solution of 1-(4-fluorophenyl)-2-oxopyrrolidine-3-carboxylic acid (0.20 g, 0.90 mmol) in a mixture of Et2O (6 mL), MeOH (2 mL), and THF (2 mL) was added (diazomethyl)trimethylsilane (1.1 mL, 2.0 M) at 0° C. The resulting mixture was stirred for 30 minutes at room temperature, quenched with AcOH, and diluted with EtOAc. The organic layer was washed with water, NaHCO3 solution (2×), and brine, dried over MgSO4, and concentrated under reduced pressure to give the desired product (0.206 g, 98%). LRMS (ESI pos) m/e 238.0 (M+1).
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