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

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.

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

ORD record

ord-07e3270837c5434b8402aeaf7011c7b2

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07687640B2