1-Bromo-3-chloropropane → 3-(3-Chloropropyloxy)-N-(benzyloxycarbonyl)morphinan

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-hydroxy-N-(benzyloxycarbonyl)morphinan 26 (3.6 mg, 0.009 mmol) in dry DMF (0.16 mL) were added potassium carbonate (4 mg, 0.028 mmol), 1-bromo-3-chloropropane (2.8 μL, 0.028 mmol) sequentially and the mixture was stirred at 50° C. After starting material disappeared on TLC, solvent was removed and column chromatography gave 3 mg (70%) of the title compound: 1H NMR (300 MHz, CDCl3) δ7.30 (5H, m); 7.00 (1H, t); 6.83 (1H, d); 6.70 (1H, d. d.); 5.10 (2H, m); 4.30 (1H, m); 4.05 (2H, t); 3.90 (1H, m); 3.79 (2H, t); 3.05 (1H, m); 2.75 (2H, m); 2.30 (1H, m); 2.15 (2H, m); 1.00˜1.80 (10H, m).

Provenance & Evidence