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

Participants

Reaction Conditions

Reaction Steps

To a suspension of 9,10-dimethoxy-13-methyl-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium; iodide (300 mg, 0.63 mmol) in anhydrous diethyl ether (100 mL) at 0° C. was added a solution of isopropenylmagnesium bromide in tetrahydrofuran (0.5 M, 18.8 mL, 9.4 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-isopropenyl-9,10-dimethoxy-13-methyl-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (90 mg, 36%). LC/MS m/e calcd for C24H23NO4 (M+H)+: 392.47, observed: 392.2; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.53 (s, 3 H) 2.13 (s, 3 H) 2.62-2.71 (m, 1 H) 2.72-2.79 (m, 1 H) 3.00-3.08 (m, 1 H) 3.13-3.21 (m, 1 H) 3.71 (s, 3 H) 3.80 (s, 3 H) 4.59 (s, 1 H) 4.77 (s, 1 H) 5.12 (s, 1 H) 6.03 (s, 2 H) 6.83 (s, 1 H) 6.93 (s, 2 H) 7.02 (s, 1 H).

Provenance & Evidence