Methyl iodide → 1-cycloheptylmethyl-4-(((2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoyl)oxy)-1-methylpiperidinium Iodide

HRID 1785250Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1785250
[F:1][C:2]1([F:32])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:31])([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:8]([O:10][CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH:18]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:13][CH2:12]2)=[O:9])[CH2:3]1.[CH3:33][I:34]>>[I-:34].[CH:18]1([CH2:17][N+:14]2([CH3:33])[CH2:13][CH2:12][CH:11]([O:10][C:8](=[O:9])[C@:7]([C@@H:4]3[CH2:5][CH2:6][C:2]([F:1])([F:32])[CH2:3]3)([OH:31])[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:16][CH2:15]2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Komponenten

3

Edukt 2

HCID 6328Methyl iodideHCID 865973021-(cycloheptyl-methyl)piperidin-4-yl (2R)-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate

Produkt 1

HCID 690728021-cycloheptylmethyl-4-(((2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoyl)oxy)-1-methylpiperidinium Iodide

Versuchsvorschrift

A solution formed by dissolving 1-(cycloheptyl-methyl)piperidin-4-yl (2R)-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate in 0.3 ml of methyl iodide at room temperature was allowed to stand for 12 hours at the same temperature, and excessive reagent was distilled off under reduced pressure. The diastereomers in the residue were separated on preparative thin layer chromatography (kieselgel™60F254, Art5744 (Merck), chloroform/methanol=5/1) to provide the title compound respectively as 3.8 mg (low polar substance) and 2.8 mg (high polar substance) of colorless oily substances.

Aufarbeitung

  1. customA solution formed
  2. distillationwas distilled off under reduced pressure
  3. customThe diastereomers in the residue were separated on preparative thin layer chromatography (kieselgel™60F254, Art5744 (Merck), chloroform/methanol=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-1d49d62c3094409599b03a48dfc5e2c3
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504432B2

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