Water → 3-(5-Hydroxy-2-naphthylsulfonyl)-3-azabicyclo[3.2.2]nonane

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Reaction Steps

The title compound was prepared from 3-(5-Acetoxy-2-naphthylsulfonyl)-3-azabicyclo[3.2.2]nonane, by dissolving the acetoxy compound in 3 ml THF and then adding 2 ml water and 2 ml saturated sodium bicarbonate solution. After stirring overnight, the solvent was evaporated and the product extracted with chloroform. After drying over magnesium sulfate, the solvent was evaporated to give an orange oil. This was purified by chromatotron using 3/1 hexane/ethyl acetate which gave a yellow solid (32 mg, 48% yield): 1H NMR (CDCl3): 8.33 (d, J=8.8, 1 H, H3), 8.25 (d, J=1.6, 1 H, H1), 7.70 (d, J=8.8, 1 H, H4), 7.49 (d, J=8.3, 1 H, H6), 7.40 (t, J=7.8, 1 H, H7), 7.02 (d, J=7.4, 1 H, H8), 6.68 (br s, 1 H, OH), 3.30 (d, J=4.2, 4 H, N(CH2R)2), 2.08 (s, 2 H, N(CH2CHR)2),1.72-1.58 (in, 8 H, alkyl H's).

Provenance & Evidence