反応 #8563

反応方程式

water

sodium borohydride

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

methanol

→

title compound

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

溶媒

1,2-dichloroethane

EDC

反応条件

後処理

1. 1
   その他At room temperature
2. 2
   その他the liquid reaction mixture
3. 3
   抽出followed by extraction with ethyl acetate
4. 4
   洗浄The organic layer was washed with water
5. 5
   乾燥a saturated aqueous solution of ammonium chloride and dried over anhydrous magnesium sulfate
6. 6
   その他After evaporating the solvent

実験手順

At room temperature, sodium borohydride (35.7 mg) was suspended in 1,2-dichloroethane (EDC, 0.2 ml). Then a solution (0.8 ml) of methyl (2S)-2-(2,3,4-trifluoroanilino)propionate (200 mg, 99.8% ee) in EDC was added to the solution. After adding methanol (137.4 mg), the liquid reaction mixture was stirred for 1 hour. 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 159.8 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.

出典