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

Participants

Reaction Conditions

Reaction Steps

7-cyano-1,2,3,4-tetrahydroisoquinoline (7 g; 44.3 mmol; 1 eq.) and potassium carbonate (10.4 g; 75.2 mmol; 1.7 eq.) were suspended in ACN (280 mL) to which was added t-butyl 3-bromopropionate (11.5 mL; 68.6 mmol; 1.05 eq.). The reaction mixture was heated to 70° C. for 24 h. Solvents were removed under vacuum and solid residue partitioned between a saturated aqueous solution of NaHCO3 and EtOAc. Organic layers was washed with brine, dried over magnesium sulfate, filtered and concentrated to afford the title compound (11.86 g; 94%) as a yellow oil. 1H NMR (DMSO-d6) δ 7.57-7.54 (m, 2H), 7.32-7.29 (m, 1H), 3.59 (s, 2H), 2.87-2.83 (t, J=5.94 Hz, 2H), 2.74-2.66 (m, 4H), 2.46-2.42 (t, J=7.01 Hz, 2H), 1.39 (s, 9H). LC/MS (Method B): 287.1 (M+H)+. HPLC (Method A) Rt 2.37 min (Purity: 96.4%).

Provenance & Evidence