Acetic Acid → 7-amino-9a-butyl-4-ethyl-6,8-difluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Participants

Reaction Conditions

Reaction Steps

The crude diketone from step 1 (about 1.05 mmol) was treated with acetic acid (5 mL) and 6N HCl (5 mL). The resulting solution was stirred and heated in an oil bath at 100° C. for 1.5 hours. After cooling to room temperature, the mixture was poured into a slurry of solid Na2CO3 in CH2Cl2, dried over MgSO4, then filtered through a pad of silica gel and the product washed off with EtOAc. The filtrate and washings were concentrated under vacuum. The crude product was purified by preparative layer chromatography on a 0.05×20×20 cm silica gel GF plate, developing with 30% EtOAc in hexanes, to afford 7-amino-9a-butyl-4-ethyl-6,8-difluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (0.16 g, 48%) as a yellow solid.

Provenance & Evidence