Potassium Carbonate → tert-butyl (7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)acetate

Participants

Reaction Steps

To a suspension of 7-cyano-1,2,3,4-tetrahydroisoquinoline (ABCR, 2 g; 12.64 mmol) and K2CO3 (3.49 g, 25.28 mmol) in CH3CN (40 mL), was added tert-butyl bromoacetate (1.96 mL; 13.27 mmol) and the reaction mixture was stirred at RT for 4 hours. Solvents were removed under vacuum and solid residue was extracted with EtOAc from a saturated aqueous solution of NaHCO3, dried over MgSO4 and evaporated under vacuum to give the title compound a as colorless oil (3.32 g; 96%). 1H NMR (DMSO-d6) δ 7.55 (m, 2H), 7.30 (m, 1H), 3.72 (s, 2H), 3.31 (s, 2H), 2.86-2.79 (m, 4H), 1.49 (s, 9H). LC/MS (Method B): 217.1 (M+1-1)+.

Provenance & Evidence