Trifluoroacetic acid → 6-Hydroxy-10-(8-phenethyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid diethylamide

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Reaction Steps

To a solution of the TFA salt of 6-methoxy-10-(8-phenethyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid diethylamide, 6e (55 mg, 0.086 mmol) in 1,2-dichloromethane (5 mL) at 0° C. was added a 1M solution of BBr3 (0.43 mL, 0.43 mmol). The mixture was allowed to stir for 2 h at rt. A saturated NaHCO3 solution was added, and the organic phase was separated. The aqueous phase was extracted with methylene chloride, and the combined organic phases were dried, filtered, and evaporated. The residue was purified via reverse phase HPLC (eluent: CH3CN in water containing 0.1% TFA) to yield 23 mg (42.8%) of title compound 6-hydroxy-10-(8-phenethyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid diethylamide, 7e as a TFA salt and as a mixture of endo and exo isomers. MS m/z=512 (M+1).

Provenance & Evidence