Methyl iodide → HCID 70239688, Verbindung

HRID 1068418Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1068418
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[C@H:10]([OH:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:24]I>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[C@H:10]([O:21][CH3:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70204515HCID 70204515, Verbindung

Produkt 1

HCID 70239688HCID 70239688, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of trans-N-t-butoxycarbonyl-4-(3-methylphenyl)-3 hydroxy piperidine (117 mg, 0.402 mmol), in DMF (2 ml) at 0° C. was added sodium hydride (24 mg of a 60% dispersion in mineral oil, 0.803 mmol). After 10 min, methyl iodide (0.050 ml, 0.803 mmol) was added and the reaction allowed to warm to room temperature over 16 hrs. The reaction was quenched by the addition of saturated NH4Cl solution (5 ml) and extraction with EtOAc. The organic extracts were washed with brine and dried, (MgSO4) and the solvent evaporated in vacuo. Chromatography of the residue (SiO2, 10-15% EtOAc in hexanes) afforded the title compound as an oil.

Aufarbeitung

  1. customThe reaction was quenched by the addition of saturated NH4Cl solution (5 ml) and extraction with EtOAc
  2. washThe organic extracts were washed with brine
  3. customdried
  4. custom(MgSO4) and the solvent evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9c44235f036a470ba3d1037f695bdad6
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248756B1

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