Reacción #8554

Ecuación de reacción

water

sodium borohydride

methyl (2S)-2-(2,3,4-trifluoroanilino)propionate

methanol

→

title compound

(2S)-2-(2,3,4-Trifluoroanilino)propanol

Disolventes

chlorobenzene

chlorobenzene

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAt room temperature
2. 2
   Otrothe liquid reaction mixture
3. 3
   Extracciónfollowed by extraction with ethyl acetate
4. 4
   LavadoThe organic layer was washed with water
5. 5
   Secadoa saturated aqueous solution of ammonium chloride and dried over anhydrous magnesium sulfate
6. 6
   OtroAfter evaporating the solvent

Procedimiento

At room temperature, sodium borohydride (35.7 mg) was suspended in chlorobenzene (0.2 ml). Then a solution (0.8 ml) of methyl (2S)-2-(2,3,4-trifluoroanilino)propionate (200 mg, 99.8% ee) in chlorobenzene was added to the solution. After adding methanol (137.4 mg), the liquid reaction mixture was stirred for 6 hours. Then water was added to the liquid reaction mixture followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of ammonium chloride and dried over anhydrous magnesium sulfate. After evaporating the solvent, the obtained residue was subjected to silica gel column chromatography to thereby give 162.9 mg (99.8% ee) of the title compound as an oily substance. The 1H-NMR and IR spectral data of this product was identical with those of the compound obtained in Example 51.

Fuente