反应详情

To a solution of benzyl 2,3-dihydroxypropylcarbamate in DMF (0.1 M) was added TBDMSCl (2.2 eq.) and imidazole (2.5 eq.) at room temperature. After stirred for 20 h, the reaction mixture was worked up with EtOAc, which was washed with water and brine. The organic layer was separated, dried and concentrated to give the crude bis-silylated product, which was dissolved in methanol (0.16 M) followed by addition of p-toluenesulfonic acid (0.1 equiv.) at 0° C. The reaction mixture was stirred for 1.5 h at the same temperature. After quenched with saturated NaHCO3 aqueous solution, the reaction mixture was extracted with EtOAc, which was washed with water and brine. The organic layer was separated, dried, concentrated, and purified on silica gel with 0-100% EtOAc/Hexanes gradient elution to provide the pure benzyl 2-(tert-butyldimethylsilyloxy)-3-hydroxypropylcarbamate.

1. washwas washed with water and brine
2. customThe organic layer was separated
3. customdried
4. concentrationconcentrated
5. customto give the crude bis-silylated product, which
6. stirringThe reaction mixture was stirred for 1.5 h at the same temperature
7. customAfter quenched with saturated NaHCO3 aqueous solution
8. extractionthe reaction mixture was extracted with EtOAc, which
9. washwas washed with water and brine
10. customThe organic layer was separated
11. customdried
12. concentrationconcentrated
13. custompurified on silica gel with 0-100% EtOAc/Hexanes gradient elution