Water → HCID 68490282, compound

Participants

Reaction Steps

A solution of 7-ethoxy-6-benzyloxytetrahydroisoquinoline acetate (293 mg, 0.86 mmol), Hunig's base (0.325 mL, 1.96 mmol) and 3,4,5-trimethoxybenzyl chloride (247 mg, 1.14 mmol) in DMF (8 mL) were heated to 80° C. overnight. Water and ethyl acetate (50 mL each) were then added to the cooled solution, the organic layer separated and washed with water (5×), brine, dried and evaporated. The desired product was isolated by column chromatography (3:2 hexane/ethyl acetate) to give the product as a clear colourless oil (340 mg, 85%) which showed 1H NMR δ 1.41 (3H, t, J 7.0), 2.63-2.80 (4H, m), 3.54 (2H, s), 3.58 (2H, s), 3.84 (3H, s), 3.84 (6H, s), 4.03 (2H, q, J 7.0), 5.09 (2H, s), 6.54 (1H, s), 6.61 (2H, s), 6.65 (1H, s) and 7.26-7.44 (5H, m). m/z HRMS [ES+] found 464.2413, C28H34NO5 (M++H) requires 464.2437.

Provenance & Evidence