Hydrogen Bromide → Pregabalin

HRID 269414Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 269414
Br.COC(=O)[NH:5][CH2:6][C@H:7]([CH2:12][C:13](=[O:23])N[C@H](C1C=CC=CC=1)C)[CH2:8][CH:9]([CH3:11])[CH3:10].[OH-:25].[Na+]>O>[CH3:11][CH:9]([CH2:8][C@H:7]([CH2:6][NH2:5])[CH2:12][C:13]([OH:23])=[O:25])[CH3:10]

Komponenten

5

Edukt 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 59832562Methyl ((S)-4-Methyl-2-[2-oxo-2-[[(S)-1-phenylethyl]amino]ethyl]pentyl]carbamate

Produkt 1

HCID 5486971PregabalinAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A flask was loaded with 47% HBr (30 ml), water (15 ml), and compound 26 (15 g), and then was heated to reflux for 3 hours. The solution was cooled to room temperature and water (30 ml) was added. An aqueous 47% sodium hydroxide solution was added to obtain pH of 3. The solution was then extracted twice with iso-butanol (37.5 ml). The organic layers were combined and Bu3N (9.5 g) was added. The mixture was cooled to 2° C. for 1 hour, then (S)-Pregabalin was filtered, and washed with of iso-butanol (10 ml). After drying at 55° C. under vacuum, (S)-Pregabalin was obtained as white crystals in a 51% yield.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. customto obtain pH of 3
  4. extractionThe solution was then extracted twice with iso-butanol (37.5 ml)
  5. additionBu3N (9.5 g) was added
  6. temperatureThe mixture was cooled to 2° C. for 1 hour
  7. filtration(S)-Pregabalin was filtered
  8. washwashed with of iso-butanol (10 ml)
  9. customAfter drying at 55° C. under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-65cd1ba7b54c41fe8e7cfe5b13526f12
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446220B2

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