Potassium Iodide → 1'-t-Butoxycarbonylspiro[benzo[c]thiophene-1-(3H),4'-piperidine]-2-oxide

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Reaction Steps

In 420 ml of chloroform, 42.0 g (0.14 mole) of the 1′-tert-butoxycarbonyl-spiro[benzo[c]thiophene-1(3H),4′-piperidine] obtained in Referential Example 1(a) were dissolved, followed by the addition of 12.7 g (0.15 mole) of sodium bicarbonate. To the resulting mixture, 28.0 g (85% content, 0.14 mole) of m-chloroperbenzoic acid were added in small portions under ice-cooling. After stirring of the mixture for 30 minutes under ice-cooling, 10 g of potassium iodide were added thereto and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with water and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure to obtain a residue. The residue was purified by chromatography on a silica gel column (eluting solvent; n-hexane: ethyl acetate=1:1), whereby 42 g of the title compound were obtained as white crystals.

Provenance & Evidence