Ammonium fluoride → HCID 11997511, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 0.154 g (4R,9aR)-7-[2-(tert-Butyl-dimethyl-silanyloxy)-vinyl]-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in and 0.154 g ammonium fluoride in 3.00 ml was heated to reflux for 4 h. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated and the organic phase was washed with brine dried over sodium sulfate and evaporated. To as solution of the residue in 3.00 ml dichloromethane was added at 0° C. 0.14 ml triethylsilane and 0.14 ml trifluoroacetic acid and the mixture was stirred at 0° C. for 2 h. To the resulting solution was added 0.7 ml trifluoroacetic acid and the mixture was allowed to thaw to room temperature over 17 h. The solvent was evaporated and the residue was partitioned between water and ethyl acetate. The phases were separated and the pH of the aqueous phase was adjusted to 12.00 by addition of 2N aqueous sodium hydroxide and the product was extracted with methylenechloride and purified by chromatography on silica gel with dichloromethane:methanol:ammonia=90:10:1 to yield 0.0047 g of the title compound as slightly yellow oil. (MS: 246.3 (M+H+))

Provenance & Evidence