7-(acetylamino)-4-bromo-9a-butyl-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one → 7-amino-4-bromo-9a-butyl-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Participants

Reaction Conditions

Reaction Steps

A solution of 7-(acetylamino)-4-bromo-9a-butyl-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (33 mg, 0.1 mmol) in methanol (0.5 mL) was diluted with aqueous 6N HCl (0.5 mL). The resulting mixture was stirred in a capped flask and heated in an oil bath at 80° C. for 40 minutes. After cooling, the mixture was partitioned between water and EtOAc. The organic solution was washed with aqueous 5% NaHCO3, water, and brine, dried over MgSO4, filtered, and concentrated under vacuum to an oil. The oil ws purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate, developing with 2:1 hexanes-EtOAc. The major UV visible band was eluted with 5% MeOH in CH2Cl2, the eluant was evaporated under vacuum, and the residue was lyophilized from benzene to provide 7-amino-4-bromo-9a-butyl-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (17 mg, 47%) as an amorphous solid.

Provenance & Evidence