Bromide ion → HCID 49806336, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 13-benzyl-9,10-dimethoxy-8,8-dimethyl-5,6,8,13-tetrahydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium; bromide (100 mg, 0.19 mmol) in methanol (10 mL) was added sodium borohydride (14 mg, 0.38 mmol) in small portions at 25° C. After stirring at 25° C. for 10 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 13-benzyl-9,10-dimethoxy-8,8-dimethyl-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (64 mg, 73%). LC/MS m/e calcd for C29H31NO4 (M+H)+: 458.57, observed: 458.3; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.42 (s, 3 H) 1.64 (s, 3 H) 2.34-2.49 (m, 2 H) 2.53-2.68 (m, 2 H) 2.75-2.85 (m, 1 H) 3.11-3.16 (m, 1 H) 3.26-3.31 (m, 1 H) 3.72 (s, 3 H) 3.80 (s, 3 H) 4.14 (s, 1 H) 5.94-5.99 (m, 3 H) 6.64 (d, J=8.34 Hz, 1 H) 6.69 (s, 1 H) 6.76 (d, J=7.07 Hz, 2 H) 6.94 (s, 1 H) 7.06-7.17 (m, 3 H).

Provenance & Evidence