1,1-dimethylethyl (1RS,2SR)-2-(2-fluoropyridin-4-yl)-2-hydroxy-1-((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)ethylcarbamate → (1RS,2SR)-2-amino-1-(2-fluoropyridin-4-yl)-3-(3-(1,1,2,2-tetrafluoroethoxy)phenyl)-1-propanol

HRID 1610501ノート

反応式

HRID 1610501 の反応式
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([OH:32])[CH:9]([NH:24]C(=O)OC(C)(C)C)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:23])([F:22])[CH:19]([F:21])[F:20])[CH:12]=2)[CH:5]=[CH:4][N:3]=1>FC(F)(F)C(O)=O>[NH2:24][CH:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:22])([F:23])[CH:19]([F:20])[F:21])[CH:12]=1)[CH:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([F:1])[CH:7]=1)[OH:32]

参加物

3

反応物 1

HCID 865932571,1-dimethylethyl (1RS,2SR)-2-(2-fluoropyridin-4-yl)-2-hydroxy-1-((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)ethylcarbamate

生成物 1

HCID 22261630(1RS,2SR)-2-amino-1-(2-fluoropyridin-4-yl)-3-(3-(1,1,2,2-tetrafluoroethoxy)phenyl)-1-propanol収率 94.1%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

Trifluoroacetic acid (10 ml) was added to 1,1-dimethylethyl (1RS,2SR)-2-(2-fluoropyridin-4-yl)-2-hydroxy-1-((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)ethylcarbamate (0.8 g, 1.73 mmol), and the mixture was stirred at room temperature for 10 min. The reaction solution was concentrated under reduced pressure, 1N aqueous sodium hydroxide solution (10 ml) was added, and the mixture was extracted with ethyl acetate (20 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. Recrystallization of the residue from ethyl acetate-hexane gave (1RS,2SR)-2-amino-1-(2-fluoropyridin-4-yl)-3-(3-(1,1,2,2-tetrafluoroethoxy)phenyl)-1-propanol (0.59 g, 93%).

後処理

  1. concentrationThe reaction solution was concentrated under reduced pressure, 1N aqueous sodium hydroxide solution (10 ml)
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate (20 ml×2)
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customRecrystallization of the residue from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-48fa9c1fcabf4ebaa071b69330c5e29d
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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