反应详情

温度

0 °C

To a solution of (4R)-4-(benzyloxymethyl)-5-(but-3-en-2-yl)oxazolidin-2-one (1.0 equiv.) in 2:1 MeOH/H2O (0.04 M) was added osmium tetroxide 4% in H2O (0.07 equiv) and sodium periodate (3.0 equiv.). After stirring for 3 hours, the white precipitate was filtered and rinsed with EtOAc. The combined filtrate was concentrated in vacuo and the residue was dissolved in EtOAc, washed with NaCl(sat.), dried over MgSO4, filtered and concentrated. The crude aldehyde was dissolved in EtOH (0.08M) and upon cooling to 0° C., sodium borohydride (2.0 equiv.) was added. After stirring for 15 hours and coming to room temperature the reaction was quenched by addition of H2O. After stirring for 20 minutes, the EtOH was removed in vacuo, EtOAc was added and the solution was washed with 1N HCl, NaHCO3(sat.) and NaCl(sat.), dried over MgSO4, filtered and concentrated yielding after purification by silica gel chromatography (4R)-4-(benzyloxymethyl)-5-(1-hydroxypropan-2-yl)oxazolidin-2-one as a 3:1 mixture of isomers (60%). LCMS (m/z): 266.1 (MH+); LC Rt=2.28 min.

1. filtrationthe white precipitate was filtered
2. washrinsed with EtOAc
3. concentrationThe combined filtrate was concentrated in vacuo
4. dissolutionthe residue was dissolved in EtOAc
5. washwashed with NaCl(sat.)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. dissolutionThe crude aldehyde was dissolved in EtOH (0.08M)
10. stirringAfter stirring for 15 hours
11. customcoming to room temperature
12. customwas quenched by addition of H2O
13. stirringAfter stirring for 20 minutes
14. customthe EtOH was removed in vacuo, EtOAc
15. additionwas added
16. washthe solution was washed with 1N HCl, NaHCO3(sat.) and NaCl(sat.)
17. dry with materialdried over MgSO4
18. filtrationfiltered
19. concentrationconcentrated
20. customyielding
21. customafter purification by silica gel chromatography (4R)-4-(benzyloxymethyl)-5-(1-hydroxypropan-2-yl)oxazolidin-2-one
22. additionas a 3:1 mixture of isomers (60%)