Imidazole → HCID 69067824, compound

Participants

Reaction Steps

A solution of (6S*,9aR*)-6-(4-fluorophenyl)-8-hydroxyoctahydroquinolizin-4-one (203 mg) in DMF (5.0 mL) was cooled to 0° C. Imidazole (262 mg), TBSCl (291 mg), and DMAP (9.42 mg) were sequentially added to the reaction solution, which was then stirred at room temperature for two hours. Saturated sodium bicarbonate water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 183 mg of (6S*,8S*,9aR*)-8-(tert-butyldimethylsilanyloxy)-6-(4-fluorophenyl)octahydroquinolizin-4-one and 31.8 mg of (6S*,8R*,9aR*)-8-(tert-butyldimethylsilanyloxy)-6-(4-fluorophenyl)octahydroquinolizin-4-one.

Provenance & Evidence