Bromide ion → HCID 49806335, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 9,10-dimethoxy-8,8-dimethyl-13-pyridin-2-ylmethyl-5,6,8,13-tetrahydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium; bromide (64 mg, 0.12 mmol) in methanol (10 mL) was added sodium borohydride (9 mg, 0.24 mmol) in small portions at 25° C. After stirring at 25° C. for 20 min, the mixture was concentrated in vacuo. The resulting residue was extracted with diethyl ether (2×50 mL), washed with water (2×25 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 9,10-dimethoxy-8,8-dimethyl-13-pyridin-2-ylmethyl-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (12 mg, 21%). LC/MS m/e calcd for C28H30N2O4 (M+H)+: 459.56, observed: 459.3; 1H NMR (400 MHz, MeOD) δ ppm 1.87 (s, 3 H) 2.03 (s, 3 H) 3.00-3.09 (m, 2 H) 3.25-3.30 (m, 1 H) 3.55 (m, 1 H) 3.82 (s, 3 H) 3.89 (s, 3 H) 4.22 (t, J=5.68 Hz, 1 H) 4.26-4.33 (m, 1 H) 5.20 (d, J=5.05 Hz, 1 H) 6.01 (d, J=4.04 Hz, 2 H) 6.75 (s, 1 H) 6.98 (s, 1 H) 7.01-7.04 (m, 2 H) 7.18 (d, J=8.59 Hz, 1 H) 7.24-7.30 (m, 1 H) 7.73 (t, J=7.71 Hz, 1 H) 8.48 (d, J=5.05 Hz, 1 H).

Provenance & Evidence