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

HRID 8458

Reaktionsgleichung

Reaktionsgleichung von HRID 8458
[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>ClC1C=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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7964ChlorobenzeneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4b3497d821714899838080df19bf8f51
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087778B2

Verknüpfte Notizen

Wird geladen…