HCID 13174066, compound → 6,7,8-Trihydroxy-1-(hydroxymethyl)-2-oxa-4-azabicyclo[3.3.1]nonan-3-one

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Reaction Steps

In 100 ml of water is dissolved 2.0 g of 9-bromo-6,7,8-trihydroxy-1-hydroxymethyl-3-oxo-2-oxa-4-azabicyclo[3.3.1]nonane, and 400 mg of palladium black is added to the solution, followed by stirring for 8 hours in a stream of hydrogen at room temperature. The catalyst is filtered off and washed with water. The filtrate and washings are combined, adjusted to pH 6 by adding a saturated aqueous solution of sodium hydrogen carbonate, and concentrated under reduced pressure. The residue is chromatographed on a column of 250 ml of MCI Gel CHP 20P (produced by Mitsubishi Chemical Ind., Ltd., Japan), followed by elution with water. The eluate is chromatographed on a column of activated carbon (250 ml), and the column is washed with water, followed by elution with a water-methanol gradient. The eluate containing the objective compound is concentrated under reduced pressure, and methanol is added to the residue, which is then allowed to stand overnight in a refrigerator to give crystals of 6,7,8-trihydroxy-1-hydroxymethyl-3-oxo-2-oxa-4-azabicyclo[3.3.1]nonane. Yield of 780 mg.

Provenance & Evidence