HCID 59574875, compound → HCID 49806337, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 8,8-diallyl-9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (68 mg, 0.16 mmol) in dry dichloromethane (50 mL) was added Grubbs' catalyst I (32 mg, 0.04 mmol) under nitrogen. The mixture was heated to reflux for 72 h at 58° C. The reaction mixture was cooled and concentrated in vacuo. Purification by Waters Automated Flash System (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 9′,10′-dimethoxy-5′,6′,13′,13a′-tetrahydrospiro[cyclopent-3-ene-1,8′-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline] (2.5 mg, 4%). LC/MS m/e calcd for C24H25NO4 (M+H)+: 392.47, observed: 392.3; 1H NMR (400 MHz, MeOD) δ ppm 2.34-2.43 (m, 2 H) 2.55-2.68 (m, 1 H) 2.68-2.75 (m, 1 H) 2.75-2.81 (m, 1 H) 2.85-2.92 (m, 1 H) 2.92-2.99 (m, 1 H) 3.03-3.10 (m, 1 H) 3.11 (d, J=3.03 Hz, 1 H) 3.14-3.18 (m, 1 H) 3.79 (s, 3 H) 3.84 (s, 3 H) 3.93-4.00 (m, 1 H) 5.78-5.83 (m, 1 H) 5.83-5.88 (m, 1 H) 5.90 (s, 2 H) 6.58 (s, 1 H) 6.78 (s, 1 H) 6.83 (m, 1 H) 6.91 (m, 1 H).

Provenance & Evidence