Reaktion #410455
ord-c8823596a44a4c9fbcc6f6d4df2647a2
Reaktionsgleichung
Edukte
Reagenzien
Lösungsmittel
Reaktionsbedingungen
Aufarbeitung
- 1Temperaturwarm to ambient temperature
- 2TemperaturHeat to reflux
- 3workup.WAITAfter 12 hours
- 4Temperaturto reflux
- 5workup.WAITAfter 12 hours
- 6Temperaturcool
- 7Sonstigethe reaction
- 8SonstigeSeparate the layers
- 9Extraktionextract the aqueous layer three times with ethyl acetate
- 10TrocknenDry the combined organic layers over Na2SO4
- 11Filtrationfilter
- 12Sonstigeevaporate in vacuo
- 13Sonstigeto give a residue
Vorschrift
Combine 1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(phenylmethyl)pyrrolidine (0.56 g, 0.77 mmol) and tetrahydrofuran (10 mL). Cool to −78° C. using a dry-ice/acetone bath. Add a solution of potassium bis(trimethylsilyl)amide (1.7 mL, 0.5 M in toluene, 0.85 mmol). After 30 minutes, warm to ambient temperature. Add tetrabutylammonium bromide (0.06 g) and 2-chloroethyl ethyl ether (0.092 g 0.85 mmol). Heat to reflux. After 12 hours, potassium bis(trimethylsilyl)amide (0.5 mL, 0.5 M in toluene) and 2-chloroethyl ethyl ether (0.5 mL) and continue to reflux. After 12 hours, cool the reaction and add water. Separate the layers and extract the aqueous layer three times with ethyl acetate. Dry the combined organic layers over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 2% triethylamine/5% methanol/ethyl acetate to give the title compound: Rf=0.32 (silica gel, 2% triethylamine/5% methanol/ethyl acetate).