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

Participants

Reaction Steps

Sodium borohydride (55 g) is added by portions to a solution of 9-bromo-6,7,8-trihydroxy-1-hydroxymethyl-3-oxo-2-oxa-4-azabicyclo[3.3.1]nonane (100 g) in water (1.3 l) at 25°-30° C. with stirring. After stirring for 2 hours at the same temperature, the reaction mixture is adjusted to pH 6-7 with acetic acid and concentrated to about 800 ml under reduced pressure. The concentrate is chromatographed on a column of activated carbon (4.8 l), and the column is washed with water (5 l) and eluted with 50% aqueous methanol. The eluate is concentrated under reduced pressure. Methanol (350 ml) is added to the residue and refluxed for 10-20 minutes to remove a methanol soluble by-product. The mixture is allowed to stand in a refrigerator overnight, and the resulting crystals are collected by filtration, followed by washing with cold methanol and drying in a desiccator under reduced pressure to give 6,7,8-trihydroxy-1-hydroxymethyl-3-oxo-2-oxa-4-azabicyclo[3.3.1]nonane (64 g).

Provenance & Evidence