tert-Butanol → HCID 67357680, compound

Participants

Reaction Steps

To a solution of 3-(1H-indol-5-yl)-3-phenyl-propionic acid CCLXXIV (0.43 g, 1.6 mmol) in tert-butanol (10 mL) was added, under nitrogen atmosphere, triethylamine (0.18 g, 1.8 mmol), followed by diphenylphosphoryl azide (0.49 g, 1.8 mmol) and the resulting mixture was heated at reflux for 3 hours. The reaction mixture was cooled to room temperature and evaporated under reduced pressure to a syrup. This residue was diluted with ethyl acetate (50 mL) and washed with an aqueous solution of citric acid (5%), water, a saturated aqueous solution of sodium bicarbonate and brine (ca. 10-20 mL of each solution). The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to a light brown film. This crude residue was purified by flash chromatography (hexane/EtOAc, 100/0 to 75/25) to give 0.10 g (19% yield) of [2-(1H-indol-5-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester CCLXXV as a colorless film.

Provenance & Evidence