Imidazole → 1-Benzyl-3-t-butyldimethylsilyloxymethylpyrrolidine

HRID 1650287

Reaktionsgleichung

Reaktionsgleichung von HRID 1650287
N1C=CN=C1.[CH2:6]([N:13]1[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].O>CN(C)C=O>[CH2:6]([N:13]1[CH2:17][CH2:16][CH:15]([CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 5176654(1-Benzylpyrrolidin-3-yl)methanol

Produkt 1

HCID 199149271-Benzyl-3-t-butyldimethylsilyloxymethylpyrrolidineAusbeute 86,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. temperaturecooling
  2. extractionextracted twice with ethyl acetate (200 ml and 100 ml)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customto give a syrup
  6. washeluted with a mixture of methanol and dichloromethane (5:95 V/V)

Quellen und Nachweise

ORD-Eintrag
ord-b1b110a41d2545c9b1e7640b3290c306
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04923857

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