Iodine → HCID 22884191, compound

Participants

Reaction Steps

To a solution of ethyl N-(p-fluorobenzyl)-N-(2-hydroxy-6-heptenyl)carbamate (1.0 g, 2.5 mmol) in methylene chloride (15 ml) was added iodine (1.26 g, 4.95 mmol) and the mixture was stirred at room temperature for 15 hours and then heated under reflux for further 7 hours. The reaction mixture was diluted with methylene chloride (50 ml) and washed successively with saturated aqueous sodium hydrogen carbonate (50 ml), 10% aqueous sodium thiosulfate (50 ml×2), saturated aqueous sodium hydrogen carbonate (50 ml) and saturated aqueous sodium chloride (50 ml), dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was chromatographed using silica gel column to give cis-6-[N-ethoxycarbonyl-N-(p-fluorobenzyl)aminomethyl]-2-iodomethyltetrahydropyrane (560 mg, yield 51%) and trans-6-[N-ethoxycarbonyl-N-(p-fluorobenzyl)aminomethyl]-2-iodomethyltetrahydropyrane (190 mg, yield 17%) from the fraction from ethyl acetate-benzene (1/30).

Provenance & Evidence