Reaktion #58578

Reaktionsgleichung

18-Crown-6

potassium cyanide

product

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

→

subtitle compound

Ausbeute 44.0%

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

Ausbeute 44.0%

Lösungsmittel

DMSO

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to room temperature
2. 2
   Extraktionextracted with ethylacetate (3×150 mL)
3. 3
   WaschenThe combined organic extracts were washed with brine (200 mL)
4. 4
   Trocknendried with MgSO4
5. 5
   Sonstigeevaporated in vacuo
6. 6
   Sonstigeto give the crude product that
7. 7
   Sonstigewas purified by column chromatography (SiO2)

Vorschrift

18-Crown-6 (5.3 g, 0.020 mol) and potassium cyanide (1.3 g, 0.020 mol) were added, respectively, to a solution of the product from step c) (6.7 g, 0.013 mol) in 50 mL of DMSO. The reaction mixture was heated at 80° C. overnight, cooled to room temperature, diluted with water (150 mL) and extracted with ethylacetate (3×150 mL). The combined organic extracts were washed with brine (200 mL), dried with MgSO4, and evaporated in vacuo to give the crude product that was purified by column chromatography (SiO2) using 1-100% ethylacetate-hexane gradient to give the subtitle compound (2.1 g, yield: 44%). MS calculated for C17H17BrN2S+H: 361, observed: 361 and 363.

Quelle