Pyridine → HCID 86754575, compound

Participants

Reaction Conditions

Reaction Steps

Pyridine (8 μl, 0.1 mmol, 0.2 equiv.) and then silver oxide (255 mg, 1.1 mmol, 2.2 equiv.) are successively added to a suspension of 10-deacetylbaccatin III (272 mg, 0.5 mmol) in a toluene/methyl iodide mixture (3/2; 2.5 ml) at room temperature. The reaction mixture is then heated to 50° C. After stirring for 24 h at 60° C., an excess of reagents is added: silver oxide (255 mg, 1.1 mmol, 2.2 equiv.), pyridine (80 μl, 1 mmol, 2 equiv.) and methyl iodide (1 ml). After heating for a further 24 h, the reaction mixture is filtered through a sinter funnel and the filtrate is diluted with ethyl acetate (40 ml). This phase is washed with brine (20 ml) separated, dried over sodium sulphate and evaporated (131 mg). According to the HPLC analysis, the crude reaction product contains 12.2% (by internal standardization of the areas) of 7,10-dimethoxy-10-deacetylbaccatin.

Provenance & Evidence