Imidazole → HCID 19914911, Verbindung

HRID 1090512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1090512
[CH2:1]([N:8]1[CH:12]([CH2:13][OH:14])[CH2:11][CH2:10][CH:9]1[CH2:15][OH:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([N:8]1[CH:12]([CH2:13][O:14][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:11][CH2:10][CH:9]1[CH2:15][OH:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 11206806(1-Benzylpyrrolidine-2,5-diyl)dimethanol

Produkt 1

HCID 19914911HCID 19914911, VerbindungAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1-benzyl-2,5-bis(hydroxymethyl)-pyrrolidine (30 g) and imidazole (27.8 g) in dimethylformamide (300 ml) was added portionwise t-butyldimethylsilyl chloride (20.4 g) at room temperature. After stirring for 1 hour at room temperature, water (0.9 l) and ethyl acetate (1.4 l) was added to the mixture. After shaking, aqueous layer was separated and extracted twice with ethyl acetate. The combined organic layer was washed with water (3 times) and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was column chromatographed on silica gel (eluent:nexane/ethyl acetate, 8:2-7:3 V/V) to give 1-benzyl-5-t-butyldimethylsilyloxymethyl-2-hydroxymethylpyrrolidine (16.8 g).

Aufarbeitung

  1. stirringAfter shaking
  2. customaqueous layer was separated
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic layer was washed with water (3 times) and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customchromatographed on silica gel (eluent:nexane/ethyl acetate, 8:2-7:3 V/V)

Quellen und Nachweise

ORD-Eintrag
ord-f14e9647e01c4174a03bb6a2cbbe376b
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05081237

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