[F:1][C:2]1[C:7]([CH:8]2[CH2:13][CH2:12]S[CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.C[N+]1([O-])CCOCC1.[S:22]([O-:25])(O)=[O:23].[Na+]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[O:23]=[S:22]1(=[O:25])[CH2:10][CH2:9][CH:8]([C:7]2[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=2)[CH2:13][CH2:12]1To a stirred mixture of 2-fluoro-3-(tetrahydro-2H-thiopyran-4-yl)pyridine (1.2 g, 6.08 mmol), 4-methylmorpholine 4-oxide (1.781 g, 15.21 mmol) in acetone/water (7:3, 30 mL) was added osmium(VIII) oxide (0.631 mL, 0.304 mmol). Stirring was continued at RT overnight. A saturated solution of sodium hydrogensulfite (10 mL) was added and stirred in 15 min., extracted with EtOAc (3×), dried over MgSO4, concentrated to give the tan solid. MS (M+1): 230.2.
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