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

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Reaction Conditions

Reaction Steps

A partial solution of 7-(acetylamino)-4-bromo-9a-butyl-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (495 mg, 1.26 mmol) in anhydrous toluene (6.3 mL) was purged with N2, treated with dichlorobis(triphenylphosphine)palladium(II) (177 mg, 0.25 mmol), purged with N2, and treated with tributyl(1-ethoxyvinyl)tin (0.600 mL, 1.9 mmol). The resulting mixture was stirred under a N2 atmosphere and heated in an oil bath at 100° C. for two hours. After cooling to room temperature, the mixture was filtered through a pad of silica gel, washing the product off with EtOAc. The filtrate and washings were evaporated under vacuum to an oil. The crude product was purified by flash chromatography on a Biotage 40S KP-Sil column, eluting with 4:1 hexanes-EtOAc (1 L) followed by 2:1 hexanes-EtOAc (1 L). The product containing fractions were concentrated under vacuum to afford 7-(acetylamino)-9a-butyl-4-(1-ethoxyvinyl)-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (238 mg, 49%) as a yellow foam.

Provenance & Evidence