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Water → (2R)-2-((S)-1-aminomethyl-2,2,2-trifluoro-1-methyl-ethylamino)-2-phenyl-ethanol

HRID 2408332
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HRID 2408332 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:24])([F:23])[C@:9]([NH:13][C@H:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:15][OH:16])([CH3:12])[C:10]#[N:11].O.C([O-])([O-])=O.[K+].[K+]>C(OCC)C>[NH2:11][CH2:10][C@@:9]([NH:13][C@H:14]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:15][OH:16])([CH3:12])[C:8]([F:23])([F:24])[F:7]
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참가 물질

6

반응물 4

HCID 962Water2회HCID 11430Potassium CarbonateHCID 16081881(2S)-3,3,3-trifluoro-2-((R)-2-hydroxy-1-phenyl-ethylamino)-2-methyl-propionitrileHCID 21226445Aluminium lithium hydride

생성물 1

HCID 16083878(2R)-2-((S)-1-aminomethyl-2,2,2-trifluoro-1-methyl-ethylamino)-2-phenyl-ethanol수율 86.6%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

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온도
4 °C

실험 절차

In a three-neck flask under argon, are added in small portions, 1.6 g of lithium aluminium hydride, on a solution cooled to 4° C., 2.5 g of (2S)-3,3,3-trifluoro-2-((R)-2-hydroxy-1-phenyl-ethylamino)-2-methyl-propionitrile in 250 mL of anhydrous ethyl ether. Strong gas evolvement is observed with a rise of the temperature to 8° C. At the end of the addition, the temperature is left to rise up to room temperature and then the reaction mixture is left with stirring for 18 h. The obtained mixture is cooled to 4° C. before adding dropwise and very slowly, 2 mL of water. Strong gas evolvement is observed with a rise of the temperature up to 12° C. To the resulting mixture maintained at 4° C., are added dropwise and very slowly, 2 mL of 15% potash and then, still dropwise and very slowly, 4 mL of water. The white precipitate formed is filtered and the obtained filtrate dried on magnesium sulfate and then concentrated under reduced pressure in order to obtain 2.2 g of (2R)-2-((S)-1-aminomethyl-2,2,2-trifluoro-1-methyl-ethylamino)-2-phenyl-ethanol including the following characteristics:

후처리

  1. customis observed with a rise of the temperature to 8° C
  2. additionAt the end of the addition
  3. waitthe temperature is left
  4. customto rise up to room temperature
  5. waitthe reaction mixture is left
  6. temperatureThe obtained mixture is cooled to 4° C.
  7. additionbefore adding dropwise
  8. customis observed with a rise of the temperature up to 12° C
  9. temperatureTo the resulting mixture maintained at 4° C.
  10. additionare added dropwise
  11. customThe white precipitate formed
  12. filtrationis filtered
  13. customthe obtained filtrate dried on magnesium sulfate
  14. concentrationconcentrated under reduced pressure in order

출처 및 근거

ORD 기록
ord-2e6a25b0d7394e6dbf3d9ce13f85f5c7
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08815853B2

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