Iodine → HCID 86755066, compound

HRID 324676Notes

Reaction equation

HRID 324676 reaction equation
C(N(CC)CC)C.[CH2:8]([N:15]1[CH2:23][C:22]2([C:24]([O:26][CH3:27])=[O:25])[CH:17]([C:18](=NN)[CH2:19][CH2:20][C:21]2([CH3:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[I:37]I.C(OCC)(=O)C>O1CCCC1>[CH2:8]([N:15]1[CH2:23][C:22]2([C:24]([O:26][CH3:27])=[O:25])[CH:17]([C:18]([I:37])=[CH:19][CH2:20][C:21]2([CH3:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 807IodineHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 86755063HCID 86755063, compound

Product 1

HCID 86755066HCID 86755066, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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-iodo-4-methyl-4-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:

Workup

  1. washthe organic phases were washed with two times 50 cm3 of a saturated aqueous sodium hydrogencarbonate solution
  2. washwashed with two times 50 cm3 of a saturated aqueous sodium thiosulphate solution
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customAfter purification by chromatography
  6. washon silica gel (230-400 mesh), elution

Sources & evidence

ORD record
ord-668b2b808b46420eb8cfbd28b3e95239
Source dataset
uspto-grants-2001_04
Patent number
US06218406B1

Reaction notes

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