Ethanolamine → 8-Bromo-9b-phenyl-2,3-dihydro-9bH-oxazolo[2,3-a]isoindol-5-one

Participants

Reaction Steps

To a solution of 2-Benzoyl-4-bromo-benzoic acid (100 mg; 0.33 mmol) in N,N-dimethylformamide (1 ml) with N,N-Diisopropylethylamine (127 μl; 0.98 mmol) is added HATU (137 mg; 0.36 mmol). It is stirred at ambient temperature for 5 minutes before ethanolamine (21 μl; 0.33 mmol) is added. After 4 hours the reaction mixture is purified via reversed phase chromatography under basic conditions. The received 5-Bromo-3-hydroxy-2-(2-hydroxy-ethyl)-3-phenyl-2,3-dihydro-isoindol-1-one is taken up in 1 ml toluene and treated with p-Toluenesulfonic acid monohydrate (3 mg; 0.02 mmol) at 120° C. for 2 days. It is purified via reversed phase chromatography under basic conditions.

Provenance & Evidence