3-Furaldehyde → 9-(8-Furan-3-ylmethyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-9H-xanthene-3-carboxylic acid diethylamide

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Reaction Steps

To a solution of 9-(8-aza-bicyclo[3.2.1]oct-3-yl)-9H-xanthene-3-carboxylic acid diethylamide, 9a (0.65 g, 1.7 mmol) in CH2Cl2 (20 mL) were added tetramethylammonium triacetoxyborohydride (0.53 g, 2.5 mmol) and 3-furaldehyde (0.17 mL, 2.0 mmol). The mixture was stirred at rt for 24 h, diluted with CH2Cl2 (10 mL), and washed with 1 N NaOH. The organic phase was dried over sodium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography (eluent: 5% 0.5 M NH3 in methanol in CH2Cl2) to yield title compound 9-(8-furan-3-ylmethyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-9H-xanthene-3-carboxylic acid diethylamide, 10a (0.25 g, 0.53 mmol). MS m/z=471.2 (MH+).

Provenance & Evidence