Triethylamine → HCID 85869821, compound

Participants

Reaction Steps

To a ice-bath cooled solution of 3-(2-hydroxyethyl)isoquinoline (Description 111; 4.85 g, 28 mmol) and triethylamine (5.07 ml, 36.4 mmol) in anhydrous dichloromethane (100 ml) was added slowly methanesulfonyl chloride (2.49 ml, 32.2 mmol), and the resulting mixture stirred at room temperature for 1 hour. The mixture was washed with water (200 ml), sat NaCl (100 ml), dried over Na2SO4, filtered and evaporated. The residue was dissolved in anhydrous N,N-dimethylformamide (100 ml) and sodium azide (2.00 g, 30.8 mmol) added and the resulting mixture stirred at room temperature for 4 days. The mixture was poured into water (400 ml), and extracted with EtOAc (3×100 ml). The combined EtOAc layers were washed with water (3×200 ml), saturated aqueous NaCl (100 ml), dried over Na2SO4, filtered and evaporated to give the title compound (5.6 g, 100%).

Provenance & Evidence