Réaction #58577

Équation de réaction

product

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

Diisopropylethylamine

dimethyl aminopyridine

TsCl

→

subtitle compound

Rendement 51.0%

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

Rendement 51.0%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwere added
2. 2
   Autreat 0° C
3. 3
   Autrewas quenched with 75 mL of 1 M HCl
4. 4
   Extractionextracted with dichloromethane (3×100 mL)
5. 5
   LavageThe combined organic extracts were washed with brine (100 mL)
6. 6
   Séchagedried with MgSO4
7. 7
   Autreevaporated in vacuo
8. 8
   Autreto give the crude product that
9. 9
   Autrewas purified by column chromatography (SiO2)

Mode opératoire

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.

Source