Imidazole → 4-{[(Tert-butyldimethylsilyl)oxy]methyl}piperidine

HRID 79173

Reaktionsgleichung

Reaktionsgleichung von HRID 79173
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.[C:9]([Si:13](Cl)([CH3:15])[CH3:14])([CH3:12])([CH3:11])[CH3:10].N1C=CN=C1.C([O-])(O)=O.[Na+].[OH-].[Na+]>ClCCl>[Si:13]([O:8][CH2:7][CH:4]1[CH2:5][CH2:6][NH:1][CH2:2][CH2:3]1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:15])[CH3:14]

Komponenten

7

Edukt 5

HCID 795ImidazoleHCID 14798Sodium HydroxideHCID 28928tert-Butyldimethylsilyl chlorideHCID 4207714-PiperidinemethanolHCID 516892Sodium Bicarbonate

Produkt 1

HCID 670219944-{[(Tert-butyldimethylsilyl)oxy]methyl}piperidineAusbeute 95,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Piperidin-4-ylmethanol (2.50 g, 21.7 mmol), t-butylchlorodimethylsilane (4.13 g, 23.9 mmol), and imidazole (1.48 g, 21.7 mmol) were dissolved in dichloromethane (25 mL) and stirred at room temperature for 18 hours. The reaction was added to aqueous NaHCO3 (200 mL, 50% saturated) and extracted with dichloromethane (3×150 mL). The combined organics were dried (MgSO4) and evaporated to give a yellow oil. Silica gel chromatography (gradient elution dichloromethane+2.5% TEA/0-10% methanol) gave a soft white solid, which was then added to 0.5 M NaOH (100 mL) and extracted with dichloromethane+10% methanol (3×100 mL). The combined organics were dried (MgSO4) and evaporated to give compound 284 as a pale yellow oil (4.75 g).

Aufarbeitung

  1. extractionextracted with dichloromethane (3×150 mL)
  2. dry with materialThe combined organics were dried (MgSO4)
  3. customevaporated
  4. customto give a yellow oil
  5. washSilica gel chromatography (gradient elution dichloromethane+2.5% TEA/0-10% methanol)
  6. customgave a soft white solid, which
  7. extractionextracted with dichloromethane+10% methanol (3×100 mL)
  8. dry with materialThe combined organics were dried (MgSO4)
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-065dcabb5fa64dfe8716560e51088083
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841312B2

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