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

HRID 1276269

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

Conditions

Temperature: 25 °C

Procedure

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).

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 1 N 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-a7d4eaf9f2ae45c7bf25936ce634fc14
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06166028

Linked notes

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