O-Methylhydroxylamine hydrochloride → HCID 86596365, compound

Participants

Reaction Steps

To a solution of 0.047 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 in 1 mL ethanol was added 0.014 g O-methylhydroxylamine hydrochloride and the mixture was stirred at ambient for 18 temperature for 18 h. The reaction mixture was partitioned between water and ethyl acetate. The organic phase was washed with 10% citric acid, 10% sodium bicarbonate and brine, then concentrated and purified by chromatography on silica gel with heptane:ethyl acetate=2:1. The product was treated with 1 mL trifluoroacetic acid at room temperature for 30 min. 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 0.027 g (4R,9aR)-7-fluoro-4-methyl-1,2,3,4,9,9a-hexahydro-2,4a,5-triaza-fluorene-6-carbaldehyde O-methyl-oxime as a light yellow solid.

Provenance & Evidence