Reaktion #1737469

Reaktionsgleichung

water

Imidazole

1-benzyl-3-hydroxymethylpyrrolidine

t-butyldimethylsilyl chloride

→

1-benzyl-3-t-butyldimethylsilyloxymethylpyrrolidine

Ausbeute 86.7%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   Extraktionextracted twice with ethyl acetate (200 ml and 100 ml)
3. 3
   Trocknendried over magnesium sulfate
4. 4
   Sonstigeevaporated under reduced pressure
5. 5
   Sonstigeto give a syrup
6. 6
   Wascheneluted with a mixture of methanol and dichloromethane (5:95 V/V)

Vorschrift

Imidazole (30.0 g) was added to a solution of 1-benzyl-3-hydroxymethylpyrrolidine (43.45 g) and t-butyldimethylsilyl chloride (48.5 g) in dimethylformamide(150 ml) under ice-cooling. The mixture was stirred at the same temperature for 2 hours and at ambient temperature for 15 hours. The mixture was poured into water (600 ml), extracted twice with ethyl acetate (200 ml and 100 ml), dried over magnesium sulfate and evaporated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (500 g) and eluted with a mixture of methanol and dichloromethane (5:95 V/V) to give 1-benzyl-3-t-butyldimethylsilyloxymethylpyrrolidine (60.15 g).

Quelle