Carbon Dioxide → Zolmitriptan

HRID 1392220Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1392220
[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][C@H:15]3[CH2:19][O:18][C:17](=[O:20])[NH:16]3)[CH:12]=2)[NH:7][C:6]=1C(O)=O.C(=O)=O.C(O)(=O)CCC(O)=O>N1C2C(=CC=CC=2)C=CC=1>[CH3:1][N:2]([CH2:3][CH2:4][C:5]1[C:13]2[CH:12]=[C:11]([CH2:14][C@@H:15]3[NH:16][C:17](=[O:20])[O:18][CH2:19]3)[CH:10]=[CH:9][C:8]=2[NH:7][CH:6]=1)[CH3:24]

Komponenten

5

Edukt 3

HCID 280Carbon DioxideHCID 1110Succinic AcidHCID 10449364Zolmitriptan-2-carboxylic Acid

Produkt 1

HCID 60857ZolmitriptanAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7047QuinolineLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

1 g (3.02 mmoles) of the (S)-3-(2-dimethylaminoethyl)-5-(2-oxo-1,3-oxazolidin-4-ylmethyl)-1H-indol-2-carboxylic acid was suspended in 10 ml of dry quinoline. 20 mg of cuprous oxide was added and the stirred suspension heated to 200° C. under dry nitrogen stream. The reaction mixture was kept at this temperature until no more CO2 was released (15-20 min.). It was left to cool to room temperature and the reaction mixture filtered through decalite. The filtrate was concentrated by vacuum distillation of the solvent, providing a residue which was dissolved with a succinic acid solution and washed three times with 15 ml of dichloromethane. The washed aqueous phase was cooled, the pH adjusted to 12 with a 40% sodium hydroxide solution and extracted three times with 20 ml of dichloromethane. The combined organic phases were dried on anhydrous sodium sulphate and evaporated to dryness. The residue was recrystallised with isopropyl alcohol to give 780 mg (90%) of zolmitriptan as a white solid.

Aufarbeitung

  1. custom(15-20 min.)
  2. waitIt was left
  3. temperatureto cool to room temperature
  4. filtrationthe reaction mixture filtered through decalite
  5. concentrationThe filtrate was concentrated by vacuum distillation of the solvent
  6. customproviding a residue which
  7. washwashed three times with 15 ml of dichloromethane
  8. temperatureThe washed aqueous phase was cooled
  9. extractionextracted three times with 20 ml of dichloromethane
  10. dry with materialThe combined organic phases were dried on anhydrous sodium sulphate
  11. customevaporated to dryness
  12. customThe residue was recrystallised with isopropyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-c521b1531a2e4ff0813ceb4c70bf95ee
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342035B2

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