Iodine → HCID 86755066, compound

Participants

Reaction Steps

2.95 cm3 of triethylamine were added to a solution of 2.8 g (7 mmol) of methyl (3aRS,4SR,7aRS)-2-benzyl-7-hydrazono-4-methyl-4-phenyloctahydroisoindole-3a-carboxylate in 80 cm3 of tetrahydrofuran and a solution of 3.6 g (14.1 mmol) of iodine in 40 cm3 of tetrahydrofuran was run in dropwise. After addition of ethyl acetate, the organic phases were washed with two times 50 cm3 of a saturated aqueous sodium hydrogencarbonate solution, washed with two times 50 cm3 of a saturated aqueous sodium thiosulphate solution, then dried over magnesium sulphate and concentrated under reduced pressure. After purification by chromatography on silica gel (230-400 mesh), elution being carried out with a cyclohexane/ethyl acetate (85/15 by volume) mixture, 2.4 g (69%) of methyl (3aRS,4SR,7aRS)-2-benzyl-7-iodo4-methyl4-phenyl-2,3,3a,4,5,7a-hexahydro-1H-isoindole-3a-carboxylate were obtained in the form of a yellow oil, the characteristic of which was as follows:

Provenance & Evidence