Sodium Hydroxide → 10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid

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Reaction Steps

To a solution of 10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid methyl ester, 2a (440 mg, 0.646 mmol) in THF (5 mL) was added 1N NaOH (5 mL), and the mixture was stirred for 3 hr at rt. The solvent was removed, the residue was dissolved in DMF and acidified with a 2N TFA solution, and purified via reverse phase HPLC to yield 295 mg (63%) of 10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid, 3a, as a TFA salt. MS m/z (MH+) 351.1.

Provenance & Evidence