Reaction #8558

Reaction equation

water

sodium borohydride

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

methanol

→

title compound

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

Solvents

methyl t-butyl ether

methyl t-butyl ether

Conditions

Workup

1. 1
   OtherAt room temperature
2. 2
   Otherthe liquid reaction mixture
3. 3
   Extractionfollowed by extraction with ethyl acetate
4. 4
   WashThe organic layer was washed with water
5. 5
   Dryinga saturated aqueous solution of ammonium chloride and dried over anhydrous magnesium sulfate
6. 6
   OtherAfter evaporating the solvent

Procedure

At room temperature, sodium borohydride (35.7 mg) was suspended in methyl t-butyl ether (0.2 ml). Then a solution (0.8 ml) of methyl (2S)-2-(2,3,4-trifluoroanilino)propionate (200 mg, 99.8% ee) in methyl t-butyl ether 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 176 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.

Source