Tetrahydrofuran → 8-allyl-13-ethyl-9,10-dimethoxy-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline

Participants

Reaction Conditions

Reaction Steps

To a suspension of 13-ethyl-9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium; iodide (200 mg, 0.4 mmol) in anhydrous diethyl ether (5 mL) at 0° C. was added a solution of allylmagnesium chloride in tetrahydrofuran (1.7 M, 2.5 mL, 4 mmol) dropwise. After stirring at 0° C. for 30 min, the reaction was quenched by adding saturated aqueous ammonium chloride solution (20 mL). The mixture was extracted with diethyl ether (2×50 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was re-crystallized from diethyl ether to afford 8-allyl-13-ethyl-9,10-dimethoxy-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (160 mg, 98%). LC/MS m/e calcd for C25H27NO4 (M+H)+: 406.5, observed: 406.2; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.18 (t, J=7.20 Hz, 3 H) 2.11-2.20 (m, 1 H) 2.25-2.35 (m, 1 H) 2.55-2.65 (m, 2 H) 2.66-2.76 (m, 2 H) 3.23-3.30 (m, 2 H) 3.80 (d, J=4.55 Hz, 6 H) 4.68-4.81 (m, 3 H) 5.63-5.75 (m, 1 H) 6.04 (d, J=11.87 Hz, 2 H) 6.85 (s, 1 H) 6.90 (s, 1 H) 6.94 (s, 2 H).

Provenance & Evidence