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Methyl iodide → (RS)-2-(5,6-Difluoro-1-methyl-1H-benzoimidazol-2-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 598566
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 598566
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[CH2:16][C:17]1[NH:21][C:20]2[CH:22]=[C:23]([F:27])[C:24]([F:26])=[CH:25][C:19]=2[N:18]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].I[CH3:29]>CN(C)C=O.O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[CH2:16][C:17]1[N:18]([CH3:29])[C:19]2[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:20]=2[N:21]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]
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Komponenten

6

Edukt 3

HCID 6328Methyl iodide3×HCID 24758Sodium hydride2×HCID 66968258(RS)-2-(5,6-Difluoro-1H-benzoimidazol-2-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 66968213(RS)-2-(5,6-Difluoro-1-methyl-1H-benzoimidazol-2-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred suspension of sodium hydride (0.46 g, 60% dispersion in mineral oil) in dimethylformamide (30 ml) at 0° C., under argon, was added (RS)-2-(5,6-difluoro-1H-benzoimidazol-2-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester, D59 (2 g) and the reaction mixture stirred for a further 30 min. before the addition of iodomethane (0.78 ml). The reaction mixture was then stirred at room temperature for 18 h, a further equivalent of iodomethane (0.35 ml) was added and stirring continued for 24 h. Further portions of sodium hydride (0.23 g, 60% dispersion in mineral oil) and iodomethane (0.35 ml) were added and the reaction stirred for an additional 24 h. After diluting with water, the aqueous layer was extracted with diethyl ether (3×). The combined organics were dried (MgSO4) and solvent removed in vacuo to afford the title compound (0.5 g).

Aufarbeitung

  1. stirringstirring
  2. waitcontinued for 24 h
  3. stirringthe reaction stirred for an additional 24 h
  4. extractionthe aqueous layer was extracted with diethyl ether (3×)
  5. dry with materialThe combined organics were dried (MgSO4) and solvent
  6. customremoved in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-067869d800f64f71b239d5786d7244c2
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07897618B2

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