Reaction #58577

Reaction equation

product

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

Diisopropylethylamine

dimethyl aminopyridine

TsCl

→

subtitle compound

Yield 51.0%

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

Yield 51.0%

Solvents

dichloromethane

Conditions

Workup

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

Procedure

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