[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH2:2][CH:3]=[CH2:4].C[N+]1([O-])CC[O:20]CC1.[OH2:24]>C1COCC1.[Os](=O)(=O)(=O)=O>[OH:24][CH:3]([CH2:4][OH:20])[CH2:2][CH2:1][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15]To a solution of 2-(but-3-enyl)isoindoline-1,3-dione (5.20 g, 25.8 mmol) in THF (86 mL) was added 4-methylmorpholine 4-oxide (4.54 g, 38.8 mmol) followed by osmium(VIII) oxide in water (3.16 mL, 0.517 mmol) dropwise. The reaction mixture was stirred at rt for 6 h. A saturated Na2S2SO3 solution was added to the reaction mixture and stirred for another 10 min. The aqueous layer was separated and extracted with EtOAc three times, and the combined organic layers were washed with water, brine and dried over Na2SO4. The solids were filtered off, and the filtrate was concentrated in vacuo to get 2-(3,4-dihydroxybutyl)isoindoline-1,3-dione which was used as-is in the next step. LC-MS (M+Na)+=258.1. 1H NMR (500 MHz, methanol-d4) δ 7.92-7.85 (m, 2H), 7.85-7.75 (m, 2H), 3.91-3.75 (m, 2H), 3.65 (dtd, J=9.1, 5.5, 3.7 Hz, 1H), 3.55-3.43 (m, 2H), 1.95-1.85 (m, 1H), 1.80-1.65 (m, 1H).
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