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Methyl iodide → Ethyl 4-(4-(cyclohexylmethyl)-4-methoxypiperidin-1-yl)benzoate

HRID 1750725
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1750725
[CH:1]1([CH2:7][C:8]2([OH:25])[CH2:13][CH2:12][N:11]([C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:28]N(C)P(N(C)C)(N(C)C)=O.CI>C1COCC1.OS([O-])(=O)=O.[Na+]>[CH:1]1([CH2:7][C:8]2([O:25][CH3:28])[CH2:13][CH2:12][N:11]([C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 12679HexamethylphosphoramideHCID 24758Sodium hydrideHCID 16109048Ethyl 4-(4-(cyclohexylmethyl)-4-hydroxypiperidin-1-yl)benzoate

Produkt 1

HCID 16109132Ethyl 4-(4-(cyclohexylmethyl)-4-methoxypiperidin-1-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
HCID 516919Sodium BisulfateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of Example 1F (380 mg) in THF (5 mL) was treated with NaH (96 mg, 60% dispersion in mineral oil), heated to 50° C. for 2 hours, and treated with hexamethylphosphoramide (1 mL) followed by MeI (1 mL). The reaction mixture was refluxed overnight, cooled to 0° C., and diluted with saturated aqueous NaHSO4 solution (10 mL). The resulting two-phase mixture was separated, the aqueous phase was extracted twice with ether, and the combined organic layers washed with water and brine. After drying over MgSO4, the mixture was concentrated in vacuo and purified by silica gel chromatography eluting with 15% ethyl acetate in hexanes.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed overnight
  2. temperaturecooled to 0° C.
  3. customThe resulting two-phase mixture was separated
  4. extractionthe aqueous phase was extracted twice with ether
  5. washthe combined organic layers washed with water and brine
  6. dry with materialAfter drying over MgSO4
  7. concentrationthe mixture was concentrated in vacuo
  8. custompurified by silica gel chromatography
  9. washeluting with 15% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-7d7f6722ea8647de8788777455c9b1cc
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09156856B2

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