Triethylamine → HCID 10317969, compound

Participants

Reaction Steps

To a solution of 2-amino-3-bromo-5,6-dimethoxybenzoic acid (0.96 g, 3 mmol) and triethylamine (0.58 ml, 4.2 mmol) in 15 ml tetrahydrofuran/ /dichloromethane (1:1) was added ethyl chloroformate (0.32 ml, 3.4 mmol) at -20° C. After stirring for 45 min. at -20° C. a solution of (2S)-(-)-1-ethyl-2-aminomethylpyrrolidine in 10 ml dichloromethane was added at -20° C. After stirring for 3 h at room temperature the mixture was washed with water and extracted with 0.5M HCl. The aqueous phase was made alkaline and extracted twice with dichloromethane. Drying (Na2SO4) and evaporation gave 0.45 g crude material which was purified by chromatography on a C18 reversed phase column with H2O/MeOH/NH3 40:60:0.3 as eluent to give 0.25 g (22%) pure product as an oil.

Provenance & Evidence