Sodium hydride → HCID 58348375, Verbindung

HRID 2192309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2192309
[CH2:1]([O:3][C:4]([C:6]1([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[N:18]12CC[CH:21]([CH2:22][CH2:23]1)[C@@H:20](O)[CH2:19]2.[H-].[Na+]>C1(C)C=CC=CC=1>[N:18]12[CH2:23][CH2:22][CH:21]([CH2:20][CH2:19]1)[C@@H:1]([O:3][C:4]([C:6]1([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])[CH2:2]2

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 914043-Quinuclidinol, (-)-HCID 583483241-Thiophen-2-yl-cycloheptanecarboxylic acid ethyl ester

Produkt 1

HCID 58348375HCID 58348375, VerbindungAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

1-Thiophen-2-yl-cycloheptanecarboxylic acid ethyl ester (Example 5c) (2.5 g) and (R) -quinuclidin-3-ol (2.08 g) were dissolved in toluene (350 mL) and sodium hydride (0.1 g) added under nitrogen. The mixture was heated to reflux for 20 hours after which the toluene was carefully distilled off to leave ˜100 mL which was cooled and washed with water (100 mL), dried (MgSO4) and evaporated. The crude product was purified by column chromatography on silica eluting with ethyl acetate/triethylamine (99/1) to afford the sub-titled compound (2.84 g).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. distillationwas carefully distilled off
  3. customto leave ˜100 mL which
  4. temperaturewas cooled
  5. washwashed with water (100 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe crude product was purified by column chromatography on silica eluting with ethyl acetate/triethylamine (99/1)

Quellen und Nachweise

ORD-Eintrag
ord-fe6cd7a005eb407dada9857f460b8b7b
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329729B2

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