HCID 69358276, compound → HCID 69358754, compound

Participants

Reaction Steps

To a solution of 5.4 g (R)-[2-(5-fluoro-2-hydroxymethyl-pyrrolo[2,3-b]pyridin-1-yl)-propyl]-carbamic acid tert-butyl ester in 55 mL dichloromethane was added 7.40 g manganese dioxide and the mixture was stirred at room temperature for 1 h. Another 7.40 g manganese dioxide was added and the mixture was stirred at room temperature for 4 h. The solids were removed by filtration over dicalite. The mother liquor was evaporated and the residue was taken up in 50 mL dichloromethane and 3.0 mL acetic acid and 10.62 g sodium triacetoxyborohydride was added. An instantaneous gas evolution took place and the mixture warmed up to ca 35° C. The mixture was stirred at ambient temperature for 18 h. To the reaction mixture was added 50 mL water. A marked gas evolution took place. The mixture was stirred at room temperature for 15 min. The phases were separated and the organic phase was evaporated to dryness and purified by chromatography on silica gel with heptane:ethyl acetate=1:1 as eluent to yield a slightly yellow oil which crystallized on standing to yield 3.80 g (R)-7-fluoro-4-methyl-3,4-dihydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester as slightly yellow crystals; m.p.: 85–87° C.

Provenance & Evidence