C[Si](C)(C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH:9]1[CH2:13][CH2:12][CH2:11][N:10]1[CH3:14].F.[K].OO.O.C([O-])([O-])=[O:28].[K+].[K+]>CO>[CH3:14][N:10]1[CH2:11][CH2:12][CH2:13][CH:9]1[C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:3]=1[OH:28]To a solution of II (0.9 g, 3.2 mmol) in 10 mL of methanol was added potassium hydrogen fluoride (0.25 g, 3.2 mmol). A solution of 30% hydrogen peroxide in water (0.88 mL, 7.7 mmol) was slowly added, and the reaction mixture was stirred and heated at 55° C. for 8 h. To the crude mixture was added K2CO3 until the pH of the solution became slightly basic (pH 8-9). After filtration of the solid and evaporation of the solvent, the crude product was purified by radial PLC (EtOAc) to yield 82% of III as a white solid. IR (neat) 2598, 23448, 1643 cm−1; 1H NMR (300 MHz, CDCl3) δ 8.68 (s, 1H), 8.58-8.56 (m, 1H), 8.12 (dd, 1H, J=1.5 and 8 Hz), 7.47 (dd, 1H, J=5.1 ans 8 Hz), 4.61 (dd, 1H, J=7.2 and 12 Hz), 3.79-3.59 (m, 2H), 2.94 (s, 3H), 2.72-2.1 (m, 4H); 13C NMR (75 MHz, CD3OD) δ 170.5, 152.8, 151.4, 141.3, 124.9, 78.3, 71.4, 54.1, 29.5, 21.1. HRMS Calcd for C10H14N2O: 179.1184. Found: 179.1190 [M+H]+. [α]D25: +23.8 (c=0.8, MeOH). IR (neat) 2598, 23448, 1643 cm−1; 1H NMR (300 MHz,) δ 8.68 (s, 1H), 8.58-8.56 (m, 1H), 8.12 (dd, 1H, J=1.5 and 8 Hz), 7.47 (dd, 1H, J=5.1 ans 8 Hz), 4.61 (dd, 1H, J=7.2 and 12 Hz), 3.79-3.59 (m, 2H), 2.94 (s, 3H), 2.72-2.1 (m, 4H); 13C NMR (75 MHz, CD3OD) δ 170.5, 152.8, 151.4, 141.3, 124.9, 78.3, 71.4, 54.1, 29.5, 21.1. HRMS Calcd for C10H14N2O: 179.1184. Found. 179.1190 [M+H]+. [α]D25+23.8 (c 8, MeOH).
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