反应 #58577

反应方程式

product

[1-Benzyl-4-(4-bromo-thiophen-2-yl)-pyrrolidin-3-yl]-methanol

Diisopropylethylamine

dimethyl aminopyridine

TsCl

→

subtitle compound

收率 51.0%

Toluene-4-sulfonic acid 1-benzyl-4-(4-bromo-thiophen-2-yl)-pyrrolidine-3-yl-methyl ester

收率 51.0%

溶剂

dichloromethane

反应条件

后处理

1. 1
   workup.ADDITIONwere added
2. 2
   其他at 0° C
3. 3
   其他was quenched with 75 mL of 1 M HCl
4. 4
   萃取extracted with dichloromethane (3×100 mL)
5. 5
   洗涤The combined organic extracts were washed with brine (100 mL)
6. 6
   干燥dried with MgSO4
7. 7
   其他evaporated in vacuo
8. 8
   其他to give the crude product that
9. 9
   其他was purified by column chromatography (SiO2)

实验过程

Diisopropylethylamine (20.2 g, 0.156 mol), dimethyl aminopyridine (320 mg, 2.6 mmol) and TsCl were (9.88 g, 0.052 mol) were added, respectively, to the product of step b) (9.1 g, 0.026 mol) in 150 mL of dichloromethane at 0° C. The reaction mixture was stirred overnight at room temperature and then was quenched with 75 mL of 1 M HCl and extracted with dichloromethane (3×100 mL). The combined organic extracts were washed with brine (100 mL), dried with MgSO4 and evaporated in vacuo to give the crude product that was purified by column chromatography (SiO2) using a 0-50% methanol-dichloromethane gradient to give the subtitle compound (6.7 g, yield: 51%). MS calculated for C23H24BrNO3S2+H: 506, observed: 506 and 508.

来源