Methyl chloroformate → HCID 22132535, compound

Participants

Reaction Steps

To a mixture of 7-bromo-1,2,3,4-tetrahydroisoquinoline (19.33 g, 0.091 mol) and triethylamine (16.6 ml, 0.119 mol) in dichloromethane (300 ml) was added a solution of methyl chloroformate (8.5 ml; 0.109 mol) in dichloromethane (30 ml), dropwise with ice cooling. Mixture was stirred for 3 h at room temperature then partitioned between saturated aqueous NaHCO3 (100 ml) and dichloromethane (100 ml). Organic phase was dried (Na2SO4) and evaporated in vacuo to give an oil. Chromatography on silica with 30% ethyl acetate-hexane as eluant gave the title compound as an oil (15.25 g, 62%).

Provenance & Evidence