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

HRID 2408332Notes

Reaction equation

HRID 2408332 reaction equation
[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]

Participants

6

Reactant 4

HCID 962Water2×HCID 11430Potassium CarbonateHCID 16081881(2S)-3,3,3-trifluoro-2-((R)-2-hydroxy-1-phenyl-ethylamino)-2-methyl-propionitrileHCID 21226445Aluminium lithium hydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
4 °C

Procedure

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:

Workup

  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

Sources & evidence

ORD record
ord-2e6a25b0d7394e6dbf3d9ce13f85f5c7
Source dataset
uspto-grants-2014_08
Patent number
US08815853B2

Reaction notes

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