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

HRID 8460

Reaction equation

HRID 8460 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>C1CCCCC1>[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 8078CyclohexaneSolvent2×

Procedure

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

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-3e1d5fafd74a45d0b8b598bf6622fd89
Source dataset
uspto-grants-2006_08
Patent number
US07087778B2

Linked notes

Loading…