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

HRID 458189Notes

Reaction equation

HRID 458189 reaction equation
[BH4-].[Na+].[F:3][C:4]1[C:16]([F:17])=[C:15]([F:18])[CH:14]=[CH:13][C:5]=1[NH:6][C@@H:7]([CH3:12])[C:8](OC)=[O:9].CO.O>C1(C)C=CC=CC=1>[F:3][C:4]1[C:16]([F:17])=[C:15]([F:18])[CH:14]=[CH:13][C:5]=1[NH:6][C@@H:7]([CH3:12])[CH2:8][OH:9]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 10125210Methyl (2S)-2-(2,3,4-trifluoroanilino)propionate

Product 1

HCID 11401466(2S)-2-(2,3,4-Trifluoroanilino)propanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

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

Workup

  1. customAt room temperature
  2. customthe liquid reaction mixture
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous solution of ammonium chloride and dried over anhydrous magnesium sulfate
  6. customAfter evaporating the solvent

Sources & evidence

ORD record
ord-dd116d2f445143d7a0150fbf7a64a68c
Source dataset
uspto-grants-2007_03
Patent number
US07189847B2

Reaction notes

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