C([OH:5])(C)(C)C.[CH:6]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[N:12][CH:13]=1)=[CH2:7].S([O-])([O-])=O.[Na+].[Na+].[OH2:27]>>[OH:27][C@H:6]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[N:12][CH:13]=1)[CH2:7][OH:5]A suspension of AD-Mix-B® (1.40 g) in water (5 ml) and t-butanol (5 ml) was cooled to 5° C. and N-(5-vinyl-pyridin-2-yl)-2,2-dimethylpropionamide (0.204 g, 1.0 mmol) was added. The mixture was stirred at 5° C. for 18 hours. The reaction mixture was then treated with sodium sulfite (3.0 g), stirred for 30 minutes and then extracted with dichloromethane. The dichloromethane extract was washed with water and brine and then dried and evaporated to afford 0.230 g (96%) of the title product as colorless crystals. mp 105-106° C. 1H NMR (CDCl3): δ=8.21 (br, 1 H); 8.10 (m, 2 H); 7.61 (d of d, 1 H); 4.70 (m, 1 H); 3.64 (m, 1 H); 3.57 (m, 1 H); 1.25 (s, 9 H). MS (Cl): m/z=239 (M+H+).
Loading…
