Imidazole → HCID 178455368, Verbindung

HRID 1173823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1173823
[CH2:1]([O:8][C:9](=[O:18])[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>C1COCC1>[CH2:1]([O:8][C:9](=[O:18])[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([O:17][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:13][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 178523817HCID 178523817, Verbindung

Produkt 1

HCID 178455368HCID 178455368, VerbindungAusbeute 98,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Combine trans-(4-hydroxy-cyclohexyl)-carbamic acid benzyl ester (16.0 g, 0.064 mol), imidazole (13.9 g, 0.10 mol), and anhydrous THF (300 mL), add tert-butyldimethylsilyl chloride (14.5 g, 0.10 mol) and stir at room temperature for 18 hours. Wash the reaction mixture with water (250 mL), saturated aqueous NaHCO3 (250 mL) and dry the organic layer over anhydrous Na2SO4. Remove the solvent and purify the residue by chromatography over silica gel (eluting with 0 to 30% EtOAc in hexane) to obtain the desired intermediate as clear oil (23.0 g, 98%).

Aufarbeitung

  1. washWash the reaction mixture with water (250 mL), saturated aqueous NaHCO3 (250 mL)
  2. dry with materialdry the organic layer over anhydrous Na2SO4
  3. customRemove the solvent
  4. custompurify the residue by chromatography over silica gel (eluting with 0 to 30% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3c038cf4aab24e0ab3de0b190b05ae9c
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834194B2

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