Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Water | HCID 962 | — |
| Edukt | Ammonium Hydroxide | HCID 14923 | — |
| Edukt | Sodium borohydride | HCID 4311764 | — |
| Edukt | 1-(2-trifluoromethyl-phenyl)-ethanone O-methyl-oxime | HCID 54513608 | — |
| Katalysator | Zirconium chloride (ZrCl4), (T-4)- | HCID 9856075 | — |
| Lösungsmittel | Tetrahydrofuran | HCID 8028 | — |
| Produkt | (1R)-1-(2-(Trifluoromethyl)phenyl)ethylamine | HCID 2782450 | 17,1% |
Reaktionsschritte
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 1N 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).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US06271236B1 |
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| Quelldatensatz | uspto-grants-2001_08 |
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| ORD ID | ord-3e697578ba174cbc989e02fcea4015bc |
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| Quellennotiz | uspto-grants-2001_08 |
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