Dimethylformamide → Ammonia

Participants

Reaction Steps

To a solution of (4R,9aR)-7-fluoro-6-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 3.3 mL dimethylformamide was added portionwise 0.100 g sodium hydride (55% in oil) and 0.27 g cyclopropyl bromide and the mixture was stirred at room temperature for 8 h. The reaction mixture was partitioned between water and ethyl acetate and the concentrated organic phase was purified by chromatography on silica gel with heptane:ethyl acetate=1:1 to yield 0.144 g of a slightly yellow oil which was taken up in 1.5 mL trifluoroacetic acid and kept at room temperature for 1 h. The solvent was evaporated and the residue was purified by chromatography on silica gel with dichloromethane:methanol:satd. ammonia (9:1:0.1) to yield 0.095 g (4R,9aR)-6-cyclopropylmethoxymethyl-7-fluoro-4-methyl-1,2,3,4,9,9a-hexahydro-2,4a,5-triaza-fluorene as a yellow orange oil.

Provenance & Evidence