Sodium borohydride → HCID 59574875, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 8,8-diallyl-9,10-dimethoxy-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (110 mg, 0.26 mmol) in methanol (20 mL) was added sodium borohydride (10 mg, 0.26 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 8,8-diallyl-9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (70 g, 64%). LC/MS m/e calcd for C26H29NO4 (M+H)+: 420.53, observed: 420.3; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.32-2.44 (m, 2 H) 2.54-2.64 (m, 1 H) 2.64-2.75 (m, 3 H) 2.90 (s, 2 H) 3.02-3.12 (m, 2 H) 3.80 (d, J=2.78 Hz, 6 H) 4.30 (d, J=2.02 Hz, 1 H) 4.69 (d, J=10.36 Hz, 1 H) 4.74-4.88 (m, 2 H) 5.01 (d, J=16.93 Hz, 1 H) 5.36-5.48 (m, 1 H) 5.58-5.72 (m, 1 H) 5.93 (s, 2 H) 6.63 (s, 1 H) 6.78-6.85 (m, 2 H) 6.94 (d, J=8.59 Hz, 1 H).

Provenance & Evidence