Heptyl-[1-(4-hydroxymethyl-phenyl)-cyclopropylmethyl]-carbamic acid tert-butyl ester → [1-(4-Formyl-phenyl)-cyclopropylmethyl]-heptyl-carbamic acid tert-butyl ester

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To a stirred solution of heptyl-[1-(4-hydroxymethyl-phenyl)-cyclopropylmethyl]-carbamic acid tert-butyl ester (850 mg, 2.24 mmol) in anhydrous diethyl ether (25 mL) under an nitrogen atmosphere was added activated manganese dioxide (Aldrich, 2.25 g). The solution was allowed to stir at room temperature for 2 hours. An additional 1 g of manganese dioxide was added and the mixture was stirred for 2 hours. The heterogeneous black mixture was filtered through a Celite plug and was washed exhaustively with methylene chloride. The clear filtrate was concentrated to a crude yellow tinged oil. The crude mixture was purified by flash chromatography (15% ethyl acetate/hexanes) to give [1-(4-formyl-phenyl)-cyclopropylmethyl]-heptyl-carbamic acid tert-butyl ester as a clear oil (640 mg, 77%).

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