Citric Acid → HCID 86596366, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2.885 g (4R,9aR)-7-fluoro-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 60 mL toluene at −78° C. was added 8.72 mL of a ca. 1.3 M solution of sec. butyl lithium in cyclohexane over 10 min. The orange mixture was stirred at −78° C. for 30 min. To the resulting viscous solution was added 1.00 mL dimethylformamide and the mixture was stirred at −78° C. for 1.5 h. To the reaction mixture was added 100 mL of a 10% citric acid solution in water. The phases were separated and the organic phase was evaporated to dryness and purified by chromatography on silica gel with heptane:ethyl acetate=2:1 to yield 0.585 g (4R,9aR)7-fluoro-6-formyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester as yellow-orange crystals; m.p.: 139–140° C. and 0.800 g (4R,9aR)-7-Fluoro-8-formyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester.

Provenance & Evidence