反应详情

Ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)ethenyl]cyclohexanecarboxylate (40 mg, 0.12 mmol), 4-methylmorpholine N-oxide (31 mg, 0.27 mmol), THF (0.8 ml), water (0.4 ml) and osmium tetroxide (0.22 ml, 0.028 mmol) were combined and the mixture was stirred at room temperature for 40 min. The mixture was then diluted with saturated sodium thiosulfate and extracted with EtOAc. The organic phase was washed with water, brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified on silica gel (EtOAc/hexane=1/1) to afford racemic ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)-1,2-dihydroxyethyl]cyclohexane-carboxylate. MS ESI calc'd. for C14H20BrNO4S [M+H]+ 378, 380. found 378, 380. 1H NMR (500 MHz, CDCl3) δ 7.55 (s, 1H), 4.15 (dd, J=5.7, 11.1, 1H), 4.07 (q, J=7.1, 2H), 3.74 (dd, J=7.0, 11.1, 1H), 2.61 (t, J=6.4, 1H), 2.20-2.10 (m, 1H), 2.05-1.84 (m, 3H), 1.85-1.70 (m, 1H), 1.60 (d, J=12.8, 1H), 1.46-1.13 (m, 5H), 1.13-1.05 (m, 1H).

1. extractionextracted with EtOAc
2. washThe organic phase was washed with water, brine
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated in vacuo
5. customThe residue was purified on silica gel (EtOAc/hexane=1/1)