Borane;tetrahydrofuran → HCID 17980132, compound

Temperature

0 °C

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).

1. additionAfter addition the reaction mixture
2. temperaturewarmed to room temperature
3. stirringstirred for 12 h
4. customThe reaction was quenched
5. additionby adding 5N HCl cautiously at 0° C. at until no gas evolution to pH=8
6. additionThe reaction mixture was diluted with water
7. extractionextracted with ether
8. washthe combined organic layers were washed with brine
9. dry with materialdried over Na2SO4
10. customThe solvate was removed in vacuo
11. custompurified by flash chromatography
12. customAfter purification

ORD record

ord-51f8bf30bf5c4faea63d66069f15e9a9

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07230011B2