反应详情

温度

0 °C

To a solution of 1′-benzyl-5-chloro-3H-spiro[2-benzofuran-1,4′-piperidin]-3-one (1.1 g, 3.35 mmol) in THF (12 mL) was added 1 M solution of borane complex in THF (7 mL, 7.0 mmol) slowly at 0° C. After addition was complete reaction mixture was kept at room temperature for 30 min, then kept at reflux overnight, cooled to 0° C. and 6M aqueous HCl (3.5 mL) was added slowly. The reaction mixture was kept at reflux for 5 h, cooled to 0° C., pH of the reaction mixture was adjusted to 10 by addition of aqueous NaOH (6M) and the whole was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulphate (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by silica gel flash chromatography (0-30% ethyl acetate in petroleum ether) to give the subtitled compound (1.0 g).

1. additionAfter addition
2. temperatureat reflux overnight
3. temperatureat reflux for 5 h
4. temperaturecooled to 0° C.
5. extractionthe whole was extracted with ethyl acetate
6. washThe organic layer was washed with water
7. dry with materialdried over sodium sulphate (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue was purified by silica gel flash chromatography (0-30% ethyl acetate in petroleum ether)