Hydrogen Bromide → Pregabalin

HRID 269413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 269413
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 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A flask was loaded with 47% HBr (12 ml), water (6 ml), and compound 26 (6 g), and then was heated to reflux for 3 hours. The solution was cooled to room temperature, and water (12 ml) was added. An aqueous 47% sodium hydroxide solution was added to obtain pH of 3. The solution was then extracted twice with isobutanol (15 ml), the combined organic layers were evaporated and fresh isobutanol was added (15 ml). Bu3N (3.8 g) was added. The mixture was cooled to 2° C. for 1 hour, then (S)-Pregabalin was filtered, and washed with of iso-butanol (3 ml). After drying at 55° C. under vacuum, (S)-Pregabalin was obtained as white crystals in a 90% 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 isobutanol (15 ml)
  5. customthe combined organic layers were evaporated
  6. additionfresh isobutanol was added (15 ml)
  7. additionBu3N (3.8 g) was added
  8. temperatureThe mixture was cooled to 2° C. for 1 hour
  9. filtration(S)-Pregabalin was filtered
  10. washwashed with of iso-butanol (3 ml)
  11. customAfter drying at 55° C. under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-35c295d295db4a1bb0a36d318f83b824
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446220B2

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