Water → 3-Hydroxymethylquinuclidine

HRID 1650879

Reaktionsgleichung

Reaktionsgleichung von HRID 1650879
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]12[CH2:14][CH2:13][CH:10]([CH2:11][CH2:12]1)[CH:9]([C:15](OC)=[O:16])[CH2:8]2.[Li].O>C(OCC)C>[N:7]12[CH2:14][CH2:13][CH:10]([CH2:11][CH2:12]1)[CH:9]([CH2:15][OH:16])[CH2:8]2

Komponenten

6

Edukt 4

HCID 962WaterHCID 2736953Methyl quinuclidine-3-carboxylateHCID 3028194LithiumHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 101300103-HydroxymethylquinuclidineAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

90 g (2.37 mole) of lithium aluminum hydride in 200 ml of diethyl ether were slowly added with stirring to a solution of 231 g (1.37 mole) of methyl quinuclidine-3-carboxylate of Example 4 in 1,000 ml of diethyl ether. Reflux was continued for 3 hours and the excess lithium alanate was carefully decomposed with 500 ml of water with proper cooling. The reaction mixture was filtered and after separation of the phases, the ether phase was dried over magnesium sulfate. Thereafter, the ether was distilled off to obtain 116 g (0.82 mole) of quinuclidine-3-methanol (60% yield) as a colorless oil.

Aufarbeitung

  1. temperatureReflux
  2. filtrationThe reaction mixture was filtered
  3. customafter separation of the phases
  4. dry with materialthe ether phase was dried over magnesium sulfate
  5. distillationThereafter, the ether was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-63c361f0fd3a413aa0f8bf4cf767ebb3
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04925942

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