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

HRID 1362721Notes

Reaction equation

HRID 1362721 reaction equation
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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-73261f19cb8346a7a0d9e1a2cd97d01f
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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