[N:1]1([C@@H:6]2[CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH:26]=[CH:25][C:24]5[C:19](=[CH:20][CH:21]=[C:22](/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH3:31])[CH:23]=5)[C:18]4=[O:32])=[CH:13][C:12]=3[F:33])[CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1C[O:37]CC1.C[N+]1([O-])CCOCC1.[OH2:47]>[Os](=O)(=O)(=O)=O>[N:1]1([C@@H:6]2[CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH:26]=[CH:25][C:24]5[C:19](=[CH:20][CH:21]=[C:22]([C@@H:27]([OH:37])[C@@H:28]([OH:47])[CH2:29][CH2:30][CH3:31])[CH:23]=5)[C:18]4=[O:32])=[CH:13][C:12]=3[F:33])[CH2:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1Firstly, osmium tetroxide (solution in tert.-butanol, 0.1 equiv.) was added to a mixture of 2-((R)-4-[1,3′]bipyrrolidinyl-1′-yl-3-fluorophenyl)-6-((Z)-pent-1-enyl)-2H-isoquinolin-1-one (0.10 g) and THF (10 mL), and then a solution of N-methyl-morpholine-N-oxide (89 mg) in water (1 mL) was added. After 48 hours the reaction mixture was concentrated and the residue was purified by preparative HPLC. In this way the product was obtained with molecular weight 479.60 (C28H34FN3O3); MS (ESI): 480 (M+H+).
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