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

HRID 1610726ノート

反応式

HRID 1610726 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1d7ab238ebbb43d690faf8371197365d
出典データセット
uspto-grants-2006_01
特許番号
US06982348B2

反応ノート

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