Potassium Acetate → 7,8-diamino-9a-butyl-6-fluoro-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

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Reaction Steps

A sample of 7-amino-9a-butyl-6-fluoro-4-methyl-8-nitro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (106 mg, 0.32 mmol) was dissolved in ethanol (13 mL) with slight warming. After cooling to room temperature, the solution was treated with KOAc (31 mg, 32 mmol) and 10% palladium on carbon (31 mg), and the resulting mixture was stirred under an atmosphere of hydrogen for 3.25 hours. The mixture was filtered through a pad of silica gel, washing the product off with 5% MeOH in CH2Cl2. The filtrate and washings were evaporated under vacuum. The residue was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate, developing with 1:1 hexanes-EtOAc. The major UV visible band was eluted with 5% MeOH in CH2Cl2, the eluant was concentrated under vacuum, and the residue was lyophilized from benzene to afford 7,8-diamino-9a-butyl-6-fluoro-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (70 mg, 72%) as an amorphous solid.

Provenance & Evidence