1,2,3,4-Tetrahydroisoquinoline → Ethyl (3,4-dihydro-1H-isoquinolin-2-yl)acetate

Participants

Reaction Steps

To a solution of 1,2,3,4-tetra-hydroisoquinoline (2.664 g, 20 mmol) and ethyl bromoacetate (3.647 g, 22 mmol) in N,N-dimethylformamide (23 mL), was added Cs2CO3 (7.168 g, 22 mmol) under N2. The mixture was stirred at room temperature for 4 hours. The solvent was removed under reduced pressure, and the remaining residue was subjected to silica gel chromatography, eluting with ethyl acetate/hexanes (33:66) to afford Intermediate 199(a) (3.39 g, 15.5 mmol) as yellow oil in 77% yield.

Provenance & Evidence