反应详情

To a solution of (3aR,4R,5R,6R,7aS)-4,5-dihydroxy-6-(hydroxymethyl)hexahydrobenzo[d]oxazol-2(3H)-one (2.23 g, 11.0 mmol) in DMF (15 mL) at room temperature was added imidazole (2.24 g, 33.0 mmol) followed by TBDMSCl (1.98 g, 13.2 mmol). The mixture was stirred at this temperature for 2.5 h. The mixture was diluted with water (150 mL) and extracted with EtOAc (5×50 mL). The extracts were dried with MgSO4 and the solvents were evaporated. The crude product was purified by silica gel column chromatography, eluted with 5% MeOH in DCM to give the product (3aR,4R,5R,6R,7aS)-6-(((tert-butyldimethylsilyl)oxy)methyl)-4,5-dihydroxyhexahydrobenzo[d]oxazol-2(3H)-one (2.57 g, 74%) as a white solid. 1H NMR (400 MHz, MeOD) δ 4.68-4.71 (m, 1H), 3.85 (dd, J=8.0 Hz, 3.2 Hz, 1H), 3.63 (dd, J=8.0 Hz, 5.2 Hz, 1H), 3.47-3.55 (m, 2H), 3.37 (t, J=7.8 Hz, 1H), 2.14 (dt, J=12.5 Hz, 2.3 Hz, 1H), 1.86-1.94 (m, 1H), 1.52-1.58 (m, 1H), 0.89 (s, 9H), 0.08 (s, 6H).

1. extractionextracted with EtOAc (5×50 mL)
2. dry with materialThe extracts were dried with MgSO4
3. customthe solvents were evaporated
4. customThe crude product was purified by silica gel column chromatography
5. washeluted with 5% MeOH in DCM