Vinyl Acetate → 5,6-Dihydroxy-2-vinyl-2-azabicyclo[2.2.1]heptan-3-one

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Reaction Steps

The intermediate 5,6-dihydroxy-2-azabicyclo[2.2.1]heptan-3-one is made by stirring a solution of 2-azabicyclo[2.2.1]hept-5-en-3-one (1.00 g, 9.16 mmole) and osmium tetroxide (2.33 g, 9.16 mmole) in pyridine (35 ml) at room temperature for 2 hours. The osmate ester is cleaved by mixing the reaction solution with a solution of sodium bisulfite (4.2 g) in water (70 ml) and pyridine (50 ml). The product is extracted from the reaction solution with 3-150 ml portions of methylene chloride. Evaporation of the dried methylene chloride gives the crude dihydroxy bicyclic amide (intermediate). The intermediate is mixed with sodium tetrachloropalladate (30 mg, 0.10 mmole) and vinyl acetate (6 ml, 66 mmole). The mixture is then refluxed for 5 days. The crude product (Compound 7) is isolated by filtration to remove the catalyst and evaporation of the excess vinyl acetate.

Provenance & Evidence