Iodine → (alphaR)-alpha-[(1S)-2-(Dimethylamino)-1-methylethyl]-alpha-ethyl-3-methoxybenzenemethanol

HRID 534703

반응식

HRID 534703 반응식
[Mg].Br[C:3]1[CH:4]=[C:5]([O:9][CH3:10])[CH:6]=[CH:7][CH:8]=1.II.[CH3:13][N:14]([CH3:22])[CH2:15][C@H:16]([CH3:21])[C:17](=[O:20])[CH2:18][CH3:19]>O1CCCC1>[CH3:13][N:14]([CH3:22])[CH2:15][C@H:16]([CH3:21])[C@:17]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1)([OH:20])[CH2:18][CH3:19]

참가 물질

6

반응물 4

HCID 807IodineHCID 169713-Bromoanisole2회HCID 5462224MagnesiumHCID 11389445(2S)-1-(Dimethylamino)-2-methylpentan-3-one

생성물 1

HCID 9942979(alphaR)-alpha-[(1S)-2-(Dimethylamino)-1-methylethyl]-alpha-ethyl-3-methoxybenzenemethanol수율 79.77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
71.5 °C

실험 절차

In a dry flask charged magnesium turning (41.0 gm 1.70 M) in tetrahydrofuran (200 ml). Under nitrogen atmosphere charged 3-Bromo anisole (20.0 gm; 0.106 M), iodine crystal (0.2 gm). Stirred and heated the reaction mass to 68-75° C. After initiation of the reaction the remaining quantity of 3-Bromo anisole (307 gm, 1.641 M) was added maintaining the reaction at reflux. Stirred and maintained the reaction mass at refluxed for 1 hrs, cooled to 25-30° C. Slowly added (2S)-1-(dimethylamino)-2-methylpentan-3-one (100.0 gm, 0.699 M) maintaining the temperature of the reaction at 25-30° C. The reaction mass was maintained for 12 hour at 25-30° C. and then quenched the reaction mass in ice cold D. M. water (1.0 Liter). Stirred and adjusted the pH of the reaction mass to 3-4 with acetic acid. Further adjusted the pH to 9-10 using ammonia solution. Stirred the reaction mass 30 minutes and extracted the reaction solution with diisopropyl ether. Combined diisopropyl ether was dried over anhydrous sodium sulphate and concentrated under reduced pressure below 40° C. to get the compound (2S,3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol.

후처리

  1. additionwas added
  2. temperaturemaintaining
  3. customthe reaction
  4. temperatureat reflux
  5. stirringStirred
  6. temperaturemaintained the reaction mass
  7. temperatureat refluxed for 1 hrs
  8. temperaturecooled to 25-30° C
  9. customthe temperature of the reaction at 25-30° C
  10. temperatureThe reaction mass was maintained for 12 hour at 25-30° C.
  11. customquenched the reaction mass in ice cold D
  12. stirringStirred
  13. stirringStirred the reaction mass 30 minutes
  14. extractionextracted the reaction solution with diisopropyl ether
  15. dry with materialCombined diisopropyl ether was dried over anhydrous sodium sulphate
  16. concentrationconcentrated under reduced pressure below 40° C.

출처 및 근거

ORD 기록
ord-1330516c3e8149ae8345c9b8dcbe237f
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853456B2

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