Triethylamine → HCID 58622231, compound

Participants

Reaction Steps

Experimental conditions analogous Example 1, 0.12 g (0.81 mmol) of quinoxaline-2-carbaldehyde, 0.24 g (1.22 mmol) of (S)-2-aminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester, 5 mL dichloromethane, and 0.25 g (1.22 mmol) of sodium triacetoxyborohydride. The reaction was quenched with aqueous sodium bicarbonate. The residue from the organic layer was purified using reverse phase HPLC, mobile phase with a gradient 10-70% acetonitrile in 40 min. Fractions containing pure product were evaporated in vacuum and dissolved in 3 mL dichloromethane. To this solution were added 0.34 mL (2.43 mmol) of triethylamine and 196 mg (0.81 mmol) of 7-methoxy-2,2-dimethyl-benzo[1,3]dioxole-5-carbonyl chloride. After 4 hours the reaction mixture was purified using flash chromatography (ethyl acetate in hexane), gave 280 mg as a yellow solid. LC-MSD, m/z for C30H36N4O6 [M+H]+: 549.7.

Provenance & Evidence