Réaction #2487459

Équation de réaction

tert-butyl[4-cyclopropyl-2-(2-oxo-2-phenylethyl)phenyl]carbamate

trifluoroacetic acid

→

title compound

Rendement 85.1%

5-Cyclopropyl-2-phenyl-1H-indole

Rendement 85.1%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   ConcentrationThe reaction mixture was concentrated under reduced pressure
3. 3
   workup.ADDITIONTo the residue were added ethyl acetate and saturated aqueous sodium hydrogen carbonate solution
4. 4
   Autreto separate the organic layer
5. 5
   LavageThe organic layer was washed with saturated brine
6. 6
   Séchagedried over anhydrous sodium sulfate
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   AutreThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Mode opératoire

To a solution of tert-butyl[4-cyclopropyl-2-(2-oxo-2-phenylethyl)phenyl]carbamate (561 mg) in dichloromethane (8 mL) was added dropwise trifluoroacetic acid (1.6 mL) under ice-cooling. The mixture was heated to room temperature, and then stirred for 23 hours. The reaction mixture was concentrated under reduced pressure. To the residue were added ethyl acetate and saturated aqueous sodium hydrogen carbonate solution to separate the organic layer. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (317 mg). 1H-NMR (CDCl3) δ ppm: 0.65-0.75 (2H, m), 0.85-1.00 (2H, m), 1.95-2.10 (1H, m), 6.70-6.80 (1H, m), 6.90-7.00 (1H, m), 7.25-7.50 (5H, m), 7.60-7.70 (2H, m), 8.24 (1H, br s).

Source