C(C1[CH:5]=[C:6]([F:11])[C:7]([Cl:10])=[N:8][CH:9]=1)C=C.C[N+]1([O-])CC[O:16]CC1.[CH2:20]1[CH2:24][O:23][CH2:22][CH2:21]1>O.[Os](=O)(=O)(=O)=O>[Cl:10][C:7]1[N:8]=[CH:9][C:22]([CH2:21][CH:20]([OH:16])[CH2:24][OH:23])=[CH:5][C:6]=1[F:11]In a flask containing a solution of 2 (1.0 g, 5.81 mmol) in THF (7.2 mL) was added H2O (3.5 mL). The mixture was cooled with an ice bath and then N-methylmorpholine N-oxide (1.0 g, 8.71 mmol) was added followed by osmium tetroxide (0.074 g, 0.291 mmol) and the mixture stirred at 0° C. for 1 h. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (50 mL×2). The organic layer was separated, washed with brine, concentrated, and chromatographed on silica gel eluted with ethyl acetate/hexanes (0-20%) to afford 0.66 g (55%) of 41 as an oil. 1HNMR (CDCl3) δ 1.92 (1 H, t, J=5.0 Hz), 2.36 (1 H, d, J=5.0 Hz), 2.80 (2 H, m), 3.52 (1 H, m), 3.73 (1 H, m), 3.93 (1 H, m), 7.46 (1 H, d, J=11.0 Hz), 8.10 (1 H, s); LC/MS (M+1) 207.
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