Galantamin → (-)-Galantamine

HRID 850695

Reaktionsgleichung

Reaktionsgleichung von HRID 850695
[CH3:1][N:2]1[CH2:19][C:17]2=[C:18]3[C:13](=[C:14]([O:20][CH3:21])[CH:15]=[CH:16]2)[O:12][C@@H:11]2[C@:5]3([CH:6]=[CH:7][C:8]([CH2:10]2)=[O:9])[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C[C@H](N(C)C)[C@H](O)C1C=CC=CC=1.C(N1C=CC=CC1N)C.[OH-].[Na+].CN1CC2=C3C(=C(OC)C=C2)OC2C3(C=CC(O)C2)CC1>CCOCC>[CH3:1][N:2]1[CH2:19][C:17]2=[C:18]3[C:13](=[C:14]([O:20][CH3:21])[CH:15]=[CH:16]2)[O:12][C@@H:11]2[C@:5]3([CH:6]=[CH:7][C@H:8]([OH:9])[CH2:10]2)[CH2:4][CH2:3]1

Komponenten

8

Edukt 6

HCID 3449GalantaminHCID 14798Sodium HydroxideHCID 64782MethylephedrineHCID 10356588NarwedineHCID 19364846n-Ethyl-2-aminopyridineHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 9651(-)-GalantamineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

(-)-Narwedine (>98% ee, 0.1 g) was added to a mixture of lithium aluminium hydride (1.2 ml of a 1.0 M solution in ether), (-)-N-methylephedrine (0.23 g) and N-ethyl-2-aminopyridine (0.31 g) in ether at 0° C., and the resulting mixture was stirred at that temperature for 4 h. Sodium hydroxide solution (10 ml of a 1.0 M solution) was added and the product extracted with dichloromethane. Evaporation of the organic phase gave (-)-galanthamine (>98% ee, 85% yield) free of epigalanthamine by GC/MS analysis.

Aufarbeitung

  1. extractionthe product extracted with dichloromethane
  2. customEvaporation of the organic phase

Quellen und Nachweise

ORD-Eintrag
ord-08359b98dfe24632af0e79f2f34302e6
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06018043

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