反应详情

温度

0 °C

A solution of tert-butyl (2R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)aziridine-1-carboxylate (prepared following literature procedures: Travins, J. M.; Etzkorn, F. A. Tetrahedron Lett. 1998, 39, 9389-9392) in THF/Et2O (1/1) (0.17 M) was cooled in an ice bath and treated dropwise over 20 min with 1 M TBAF in THF (1.05 eq). The resulting solution was stirred in the ice bath for 30 min, before being quenched by the addition of sat. aq. NaHCO3 and extracted into Et2O/PE (4/1). The organic layers were collected, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was taken up in dry DCM (0.17 M) and Et3N (1.3 eq) introduced prior to cooling to 0° C. DMAP (0.1 eq) and 4-nitrobenzenesulfonyl chloride (1.1 eq) were added and the resulting mixture left to stir at RT overnight. The reaction mixture was diluted with DCM and washed with sat. aq. NaHCO3, water and brine before drying over Na2SO4, filtering and concentrating in vacuo. The crude was purified by FC (PE/EtOAc 8:2) to afford the title compound as an off-white solid (57%). (ES+) m/z 359 (M+H)+.

1. custombefore being quenched by the addition of sat. aq. NaHCO3
2. extractionextracted into Et2O/PE (4/1)
3. customThe organic layers were collected
4. washwashed with brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. waitthe resulting mixture left
9. washwashed with sat. aq. NaHCO3, water and brine
10. dry with materialbefore drying over Na2SO4
11. filtrationfiltering
12. concentrationconcentrating in vacuo
13. customThe crude was purified by FC (PE/EtOAc 8:2)