Reacción #58577

Ecuación de reacción

product

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

Diisopropylethylamine

dimethyl aminopyridine

TsCl

→

subtitle compound

Rendimiento 51.0%

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

Rendimiento 51.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added
2. 2
   Otroat 0° C
3. 3
   Otrowas quenched with 75 mL of 1 M HCl
4. 4
   Extracciónextracted with dichloromethane (3×100 mL)
5. 5
   LavadoThe combined organic extracts were washed with brine (100 mL)
6. 6
   Secadodried with MgSO4
7. 7
   Otroevaporated in vacuo
8. 8
   Otroto give the crude product that
9. 9
   Otrowas purified by column chromatography (SiO2)

Procedimiento

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.

Fuente