tert-Butanol → 2-(2-Fluorophenyl)propan-2-amine

HRID 1446577Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446577
C(O)(C)(C)C.C1(P([N:20]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C.[F:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37]([CH3:42])(C)[C:38](O)=O>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[F:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37]([NH2:20])([CH3:42])[CH3:38]

Komponenten

8

Edukt 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 259167252-(2-Fluorophenyl)-2-methylpropanoic acid

Produkt 1

HCID 135695202-(2-Fluorophenyl)propan-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

t-Butyl alcohol (30 mL), diphenylphosphoryl azide (1.63 mL) and triethylamine (1.05 mL) were added to a solution of 2-(2-fluorophenyl)-2-methylpropionic acid (1.15 g) in toluene (60 mL), and the reaction solution was heated to reflux overnight. The reaction solution was returned to room temperature, and water and ethyl acetate were added thereto and the organic layer was partitioned. The resulting organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. 10 mL of 5 N hydrochloric acid was added to a solution of the residue in THF (5 mL), and the reaction solution was heated to reflux for 3 hours. The reaction solution was returned to room temperature, made basic with 5 N sodium hydroxide, and then extracted with ethyl acetate. The resulting organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 735 mg of the title compound. The physical properties of the compound are as follows.

Aufarbeitung

  1. temperaturethe reaction solution was heated
  2. temperatureto reflux overnight
  3. customwas returned to room temperature
  4. customthe organic layer was partitioned
  5. dry with materialThe resulting organic layer was dried over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. addition10 mL of 5 N hydrochloric acid was added to a solution of the residue in THF (5 mL)
  8. temperaturethe reaction solution was heated
  9. temperatureto reflux for 3 hours
  10. customwas returned to room temperature
  11. extractionextracted with ethyl acetate
  12. dry with materialThe resulting organic layer was dried over magnesium sulfate
  13. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-45c9d623bf66403485a865ca95ba5b9d
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07667041B2

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