反応 #58577

反応方程式

product

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

Diisopropylethylamine

dimethyl aminopyridine

TsCl

→

subtitle compound

収率 51.0%

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

収率 51.0%

溶媒

dichloromethane

反応条件

後処理

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

実験手順

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.

出典