Dimethylformamide → 3-Chloro-2-formyl-8-methyl-8-azabicyclo[3.2.1]oct-2-ene oxalate

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To a dimethylformamide (4.5 ml, 60 mmol) at 0° C. was added phosphorous oxychloride (3 ml, 30 mmol). Tropinone (2 g, 13 mmol) was added, and the reaction mixture heated to 70° C. for 1/2 h. After cooling, crushed ice was added and then solid potassium carbonate until alkaline reaction. The water solution was extracted with ether (3×30 ml). The ether extracts were dried and evaporated. The crude compound was purified by column chromatography with acetone as eluent. The title compound was precipitated with a 1M oxalic acid acetone solution, filtered and dried. M.p. 136°-137° C. decomposes.

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