Hydrogen Bromide → Pregabalin

HRID 269413

반응식

HRID 269413 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 5486971Pregabalin수율 90%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-35c295d295db4a1bb0a36d318f83b824
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446220B2

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