Water → Bis(tropan-3-yl) succinate

HRID 650612

Reaktionsgleichung

Reaktionsgleichung von HRID 650612
[CH3:1][N:2]1[CH:6]2[CH2:7][CH:8]([OH:10])[CH2:9][CH:3]1[CH2:4][CH2:5]2.[C:11](Cl)(=[O:17])[CH2:12][CH2:13][C:14](Cl)=[O:15].[OH2:19].[OH-].[Na+]>C(Cl)Cl>[C:11]([O:17][CH:8]1[CH2:7][C@H:6]2[N:2]([CH3:1])[C@H:3]([CH2:4][CH2:5]2)[CH2:9]1)(=[O:19])[CH2:12][CH2:13][C:14]([O:10][CH:8]1[CH2:9][C@H:3]2[N:2]([CH3:1])[C@H:6]([CH2:5][CH2:4]2)[CH2:7]1)=[O:15]

Komponenten

6

Edukt 4

HCID 962WaterHCID 84248-Methyl-8-azabicyclo(3.2.1)octan-3-olHCID 10970Succinyl chlorideHCID 14798Sodium Hydroxide

Produkt 1

HCID 11824654Bis(tropan-3-yl) succinateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 14.1 g (100 mmol) of tropine in 50 mL of methylene chloride is added dropwise 7.75 g (50 mmol) of succinyl chloride in 100 mL of methylene chloride with cooling in an ice bath. Then the mixture is allowed to warm to room temperature. After the reaction mixture is poured into 200 mL of cold water, the aqueous layer is adjusted to pH 10-11 with 6 N NaOH aqueous solution and extracted with chloroform. The resulting oil is purified by column chromatography (silica gel, 20% methanol in chloroform) to yield 11.8 g (65%) of bis-tropan-3-yl succinate as a thick oil.

Aufarbeitung

  1. temperaturewith cooling in an ice bath
  2. extractionextracted with chloroform
  3. customThe resulting oil is purified by column chromatography (silica gel, 20% methanol in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-45c38c573f15441f8d69561738e12d25
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06274623B1

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