反应 #586173

反应方程式

tert-butyl (2R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)aziridine-1-carboxylate

TBAF

THF

4-nitrobenzenesulfonyl chloride

→

title compound

收率 57.0%

tert-butyl (2R)-2-({[(4-nitrophenyl)sulfonyl]oxy}methyl)aziridine-1-carboxylate

收率 57.0%

溶剂

THF Et2O

DCM

反应条件

后处理

1. 1
   其他before being quenched by the addition of sat. aq. NaHCO3
2. 2
   萃取extracted into Et2O/PE (4/1)
3. 3
   其他The organic layers were collected
4. 4
   洗涤washed with brine
5. 5
   干燥dried over Na2SO4
6. 6
   过滤filtered
7. 7
   浓缩concentrated in vacuo
8. 8
   workup.WAITthe resulting mixture left
9. 9
   洗涤washed with sat. aq. NaHCO3, water and brine
10. 10
    干燥before drying over Na2SO4
11. 11
    过滤filtering
12. 12
    浓缩concentrating in vacuo
13. 13
    其他The crude was purified by FC (PE/EtOAc 80:20)

实验过程

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 TEA (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 80:20) to afford the title compound as an off-white solid (57%). (ES+) m/z 359 (M+H)+

来源