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

HRID 1276269

반응식

HRID 1276269 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
25 °C

실험 절차

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 1 N 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).

후처리

  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 1 N 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

출처 및 근거

ORD 기록
ord-a7d4eaf9f2ae45c7bf25936ce634fc14
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06166028

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