Borane;tetrahydrofuran → HCID 17980132, compound

Participants

Reaction Conditions

Reaction Steps

8-Methoxy-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione (3.0 g, 13.8 mmol), was added to BH3-THF (1.0 M, 30 mL, 30 mmol) dropwise at 0° C. After addition the reaction mixture was stirred 0° C. for 5 h, then warmed to room temperature and stirred for 12 h. The reaction was quenched by adding 5N HCl cautiously at 0° C. at until no gas evolution to pH=8. The reaction mixture was diluted with water, extracted with ether, the combined organic layers were washed with brine, dried over Na2SO4. The solvate was removed in vacuo and purified by flash chromatography using hexanes/ethyl acetate (9:1). After purification, 1.3 g (50%) of title compound was obtained: 1H NMR (300 MHz, CDCl3) 2.21-2.27 (m, 2H), 2.96 (t, 2H, J=6.1 Hz), 3.83 (s, 3H), 4.13 (t, 2H, J=5.8 Hz), 6.36 (d, 1H, J=2.8 Hz), 6.62 (d, 1H, J=1.4 Hz), 6.91 (d, 1H, J=2.2 Hz), 7.05 (d, 1H, J=2.7 Hz).

Provenance & Evidence