Carbon tetrabromide → HCID 11543102, compound

Participants

Reaction Steps

To a solution of 0.068 g (4R,9aR)-7-fluoro-8-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 3 mL of dichloromethane was added 0.0995 g tetrabromomethane and 0.0786 g triphenylphosphine and the mixture was stirred at ambient temperature for 2.5 h The reaction mixture was concentrated and the residue was purified by chromatography on silica gel with a mixture of heptane:ethyl acetate (1:1) to yield 0.0695 g of a slightly yellow oil. This oil was dissolved in 1 mL tetrahydrofuran and 3.0 mg palladium acetate was added. To the resulting mixture was added 0.05 mL polymethylhydrosiloxane and the mixture was stirred at room temperature for 0.5 h. The reaction mixture was partitioned between water and ethyl acetate. The organic phase was washed with water and dried over sodium sulfate and evaporated. The residue was dissolved in 0.60 mL trifluoroacetic acid and stirred at room temperature for 0.5 h. The solvent was evaporated and the residue was purified by chromatography on silica gel with dichloromethane:methanol:ammonia (25% in water) (9:1:0.1) to yield 0.032 g (4R,9aR)-7-fluoro-4,8-dimethyl-1,2,3,4,9,9a-hexahydro-2,4a,5-triaza-fluorene as a slightly yellow oil.

Provenance & Evidence