Boron trifluoride etherate → HCID 22282663, compound

Temperature

-20 °C

A solution of 2,3,7,8-tetrahydro-1H-furo[2,3-g]indole-2,3-dione (9.05 g, 47.9 mmol) in tetrahydrofuran (100 mL) was stirred at −20° C. under an argon atmosphere. Solid sodium borohydride was added portionwise and the reaction was stirred for 20 min at −20° C. Boron trifluoride etherate (11.9 mL, 96 mmol) was added dropwise over 90 min, then the mixture was warmed to 0° C. and stirred for 1 h. The reaction was quenched with water (100 mL) and the solution was extracted with ethyl acetate (3×150 mL). The organic extracts were combined, dried (magnesium sulphate) and concentrated in vacuo to afford a yellow solid which was purified by column chromatography [SiO2; heptane-ethyl acetate (5:1)] to afford the title compound (3.2 g, 42.8%); analytical data as described above.

1. temperaturethe mixture was warmed to 0° C.
2. stirringstirred for 1 h
3. customThe reaction was quenched with water (100 mL)
4. extractionthe solution was extracted with ethyl acetate (3×150 mL)
5. dry with materialdried (magnesium sulphate)
6. concentrationconcentrated in vacuo
7. customto afford a yellow solid which
8. customwas purified by column chromatography [SiO2; heptane-ethyl acetate (5:1)]

ORD record

ord-047798573e76485e9ab064388fcec71f

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07166613B2