반응 #58577

반응 방정식

product

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

Diisopropylethylamine

dimethyl aminopyridine

TsCl

→

subtitle compound

수율 51.0%

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

수율 51.0%

용매

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONwere added
2. 2
   기타at 0° C
3. 3
   기타was quenched with 75 mL of 1 M HCl
4. 4
   추출extracted with dichloromethane (3×100 mL)
5. 5
   세척The combined organic extracts were washed with brine (100 mL)
6. 6
   건조dried with MgSO4
7. 7
   기타evaporated in vacuo
8. 8
   기타to give the crude product that
9. 9
   기타was purified by column chromatography (SiO2)

실험 절차

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.

출처