Water → (1R)-1-(2-(Trifluoromethyl)phenyl)ethylamine
Reaction equation
[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]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
5 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 IN 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)
Workup
- temperatureThe reaction mixture is then cooled to 0° C.
- extractionthe solution is extracted twice with ethyl acetate
- washThe organic portion is washed twice with IN hydrochloric acid
- extractionextracted twice with ethyl acetate
- washThe organic layer is then washed with saturated aqueous sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent is removed under reduced pressure
Sources & evidence
- ORD record
- ord-f68d87eb7f324c3ea19bc2f1e5eccb06
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06403617B1
Reaction notes
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