Sodium Hydroxide → (1RS,2SR)-2-amino-3-[3-(1,1-difluoroethyl)phenyl]-1-(4-fluorophenyl)-1-propanol

HRID 1610726노트

반응식

HRID 1610726 반응식
[F:1][C:2]([C:5]1[CH:6]=[C:7]([CH:22]=[CH:23][CH:24]=1)[CH2:8][CH:9]1[CH:13]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[O:12]C(=O)[NH:10]1)([F:4])[CH3:3].[OH-].[Na+]>C(O)C.O>[NH2:10][CH:9]([CH2:8][C:7]1[CH:22]=[CH:23][CH:24]=[C:5]([C:2]([F:4])([F:1])[CH3:3])[CH:6]=1)[CH:13]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[OH:12]

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 22261676(4RS,5SR)-4-[3-(1,1-difluoroethyl)benzyl]-5-(4-fluorophenyl)-1,3-oxazolidin-2-one

생성물 1

HCID 22261599(1RS,2SR)-2-amino-3-[3-(1,1-difluoroethyl)phenyl]-1-(4-fluorophenyl)-1-propanol수율 88%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a solution of (4RS,5SR)-4-[3-(1,1-difluoroethyl)benzyl]-5-(4-fluorophenyl)-1,3-oxazolidin-2-one (3.83 g, 12.5 mmol) in ethanol (100 ml) was added 8N aqueous sodium hydroxide solution (7.8 ml, 39.0 mmol), and the mixture was heated under reflux for 5 hrs. After completion of the reaction, the mixture was diluted with water, and extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was recrystallized from (hexane-ethyl acetate) to give (1RS,2SR)-2-amino-3-[3-(1,1-difluoroethyl)phenyl]-1-(4-fluorophenyl)-1-propanol (3.08 g, 88%) as colorless crystals.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hrs
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from (hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-1d7ab238ebbb43d690faf8371197365d
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982348B2

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