Water → (1R)-1-(2-(Trifluoromethyl)phenyl)ethylamine

HRID 649877ノート

反応式

HRID 649877 の反応式
[BH4-].[Na+].CO[N:5]=[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([F:17])([F:16])[F:15])[CH3:7].O.[OH-].[NH4+]>O1CCCC1.[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[F:15][C:14]([F:16])([F:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH:6]([NH2:5])[CH3:7]

参加物

7

反応物 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 4311764Sodium borohydrideHCID 545136081-(2-trifluoromethyl-phenyl)-ethanone O-methyl-oxime

生成物 1

HCID 2782450(1R)-1-(2-(Trifluoromethyl)phenyl)ethylamine収率 17.1%

試薬・触媒・溶媒 2

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
25 °C

実験手順

Sodium borohydride (1.17 g) is added slowly to a flask containing zirconium tetrachloride (1.8 g) in tetrahydrofuran (27 mL). A solution of 1-(2-trifluoromethyl-phenyl)-ethanone O-methyl-oxime (1.34 g) in tetrahydrofuran (7.7 mL) is added and the resulting solution is stirred at 25° C. for 12 hours. The reaction mixture is then cooled to 0° C. and water (16 mL) is slowly added. Excess ammonium hydroxide is added and the solution is extracted twice with ethyl acetate. The organic portion is washed twice with 1N hydrochloric acid. The aqueous (acid) layer is basified with sodium hydroxide and extracted twice with ethyl acetate. The organic layer is then washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent is removed under reduced pressure to provide the desired product as a yellow oil (0.20 g).

後処理

  1. temperatureThe reaction mixture is then cooled to 0° C.
  2. extractionthe solution is extracted twice with ethyl acetate
  3. washThe organic portion is washed twice with 1N hydrochloric acid
  4. extractionextracted twice with ethyl acetate
  5. washThe organic layer is then washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent is removed under reduced pressure

出典と根拠

ORDレコード
ord-3e697578ba174cbc989e02fcea4015bc
出典データセット
uspto-grants-2001_08
特許番号
US06271236B1

反応ノート

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