Methyl iodide → HCID 18423446, Verbindung

HRID 1282013Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1282013
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][C:17]([OH:20])([CH3:19])[CH3:18])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:21]I>CN(C=O)C>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][C:17]([O:20][CH3:21])([CH3:19])[CH3:18])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18423490358625-61-3

Produkt 1

HCID 18423446HCID 18423446, VerbindungAusbeute 90,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a mixture of 0.06 g (2.5 mmol) of NaH in 5 mL of DMF at rt was added a solution of 0.1 g (0.39 mmol) of 1-t-butoxycarbonyl-4-(2-hydroxy-2-methyl-1-propyl)piperidine in 3 mL of DMF. After stirring for 20 min, 0.22 mL (3.5 mmol) of CH3I was added to the reaction mixture and the reaction mixture was stirred for 2 h. The reaction mixture was quenched with water and extracted with EtOAc. The combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate, 9:1) to give 0.096 g of the title compound.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 2 h
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with EtOAc
  4. washThe combined organic fractions were washed with sat'd NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by chromatography (silica, hexanes:ethyl acetate, 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-a556bcf4eb524dec9f2bdb1ac6ce5fb4
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06455548B2

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