Trifluoroacetic acid → 2-Acetyl-3-methyl-8-azabicyclo[3.2.1]oct-2-ene

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Reaction Steps

A solution of trifluoroacetic acid (18.8 mmol, 2.13 mL) and 2-Acetyl-3-methyl-8-(tert-butyloxycarbonyl)-8-azabicyclo [3.2.1]oct-2-en (0.49 g, 1.88 mmol) was stirred at room temperature for about 0.5 hour. The solution was concentrated three times under reduced pressure after the addition of hexane to remove excess trifluoroacetic acid. A concentrated solution of sodium carbonate was added to the residue to form a basic solution. The solution was extracted with methylene chloride, dried using sodium sulfate and purified by bulb-to-bulb distillation (80° C. (1.0 mmHg)) to give 2-acetyl-3-methyl-8-azabicyclo [3.2.1]oct-2-ene.

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