1,1'-Carbonyldiimidazole → (Quinolin-4-yl)-carbamic acid 2-(6,7-dimethoxy-1-phenethyl-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl ester

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Reaction Steps

To a solution of 2-(6,7-dimethoxy-1-phenethyl-3,4-dihydro-1H-isoquinolin-2-yl)-ethanol (example 113.1, 29.7 mg, 0.087 mmol) in THF (1 mL) is added CDI (28.2 mg, 0.174 mmol, 2.0 eq). The reaction mixture is stirred at rt for 3 h, and then 4-amino-quinoline (example C3, 14 mg, 0.1 mmol) is added. To the resulting solution is added in a single portion NaHMDS (2 M in THF, 218 μL, 0.44 mmol). The reaction mixture is stirred at rt for 30 min, then H2O/AcOH (9:1, 0.4 mL) is added. The reaction mixture is evaporated and the residue purified by preparative HPLC to provide the title compound.

Provenance & Evidence