반응 #8554

반응 방정식

water

sodium borohydride

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

methanol

→

title compound

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

용매

chlorobenzene

chlorobenzene

반응 조건

후처리

1. 1
   기타At room temperature
2. 2
   기타the liquid reaction mixture
3. 3
   추출followed by extraction with ethyl acetate
4. 4
   세척The organic layer was washed with water
5. 5
   건조a saturated aqueous solution of ammonium chloride and dried over anhydrous magnesium sulfate
6. 6
   기타After evaporating the solvent

실험 절차

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.

출처