Imidazole → 4-Piperidineethanol TBS

HRID 79179

Reaktionsgleichung

Reaktionsgleichung von HRID 79179
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1.[C:10]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])([CH3:12])[CH3:11].N1C=CN=C1.C([O-])([O-])=O.[K+].[K+]>ClCCl>[Si:14]([O:9][CH2:8][CH2:7][CH:4]1[CH2:5][CH2:6][NH:1][CH2:2][CH2:3]1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:16])[CH3:15]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 11430Potassium Carbonate2×HCID 28928tert-Butyldimethylsilyl chlorideHCID 739534-Piperidineethanol

Produkt 1

HCID 162207594-Piperidineethanol TBSAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-(piperidin-4-yl)ethanol (2.00 g, 15.5 mmol), t-butylchlorodimethylsilane (2.57 g, 17.0 mmol), and imidazole (1.05 g, 15.5 mmol) were taken up in dichloromethane (15 mL) and stirred for 22 hours. This solution was added to aqueous K2CO3 (80 mL) and extracted with dichloromethane (3×30 mL). The combined organics were dried (MgSO4) and evaporated to give a pale yellow oil. Silica gel chromatography (gradient elution dichloromethane+2.5% TEA/0-10% methanol) afforded a white solid. This solid was added to aqueous K2CO3 (60 mL) and extracted with dichloromethane+10% methanol (3×30 mL), the organics dried (MgSO4) and evaporated to give compound 292 as a yellow oil (3.24 g, 86%).

Aufarbeitung

  1. extractionextracted with dichloromethane (3×30 mL)
  2. dry with materialThe combined organics were dried (MgSO4)
  3. customevaporated
  4. customto give a pale yellow oil
  5. washSilica gel chromatography (gradient elution dichloromethane+2.5% TEA/0-10% methanol)
  6. customafforded a white solid
  7. extractionextracted with dichloromethane+10% methanol (3×30 mL)
  8. dry with materialthe organics dried (MgSO4)
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-823f08d8e54043b5ae2c31a6bb0c32cb
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841312B2

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