反应 #1876843

反应方程式

BH3.THF THF

4-[(2-methylthio-ethyl)-(4-fluoro-benzoyl)-amino]-N-acetyl-benzenesulfonamide

→

4-[(2-methylthio-ethyl)-(4-fluoro-benzyl)-amino]-N-ethyl-benzenesulfonamide

收率 60.6%

溶剂

THF

反应条件

后处理

1. 1
   其他the excess BH3 was quenched by addition of 0.1 M HCl
2. 2
   其他by partitioning the mixture between CH2Cl2 and NaHCO3
3. 3
   干燥The organic layer was dried (Na2SO4)
4. 4
   过滤filtered
5. 5
   其他evaporated in vacuo
6. 6
   其他the residue was purified by MPLC (CH2Cl2 to 90:10 CH2Cl2/EtOAc)

实验过程

A solution of 1 M BH3.THF/THF (7.0 mL, 7.0 mmol) was added to a stirring solution of 4-[(2-methylthio-ethyl)-(4-fluoro-benzoyl)-amino]-N-acetyl-benzenesulfonamide (0.29 g, 0.69 mmol) in THF (8 mL). After 18 h, the excess BH3 was quenched by addition of 0.1 M HCl; followed by partitioning the mixture between CH2Cl2 and NaHCO3. The organic layer was dried (Na2SO4), filtered, evaporated in vacuo, and the residue was purified by MPLC (CH2Cl2 to 90:10 CH2Cl2/EtOAc) to afford 0.16 g (59%) of 4-[(2-methylthio-ethyl)-(4-fluoro-benzyl)-amino]-N-ethyl-benzenesulfonamide as a colorless glass; 1H NMR δ 1.09 (t, 3H, J=7.5), 2.16 (s, 3H), 2.74 (m, 2H), 2.96 (m, 2H), 3.67 (m, 2H), 4.37 (t, 1H, J=6.0), 4.62 (s, 2H), 6.69 (d, 2H, J=9.0), 7.04 (dd, 2H, J=4.5, 7.5), 7.15 (dd, 2H, J=6.0, 9.0), 7.66 (d, 2H, J=7.5).

来源