Iodine → HCID 86755062, compound

HRID 849609Notes

Reaction equation

HRID 849609 reaction equation
[I:1]I.[CH3:3][O:4][C:5]([C:7]12[CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH3:23])[CH2:14][CH2:13][C:12](=NN)[CH:11]1[CH2:10][N:9]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:8]2)=[O:6].C(OCC)(=O)C>O1CCCC1>[CH3:3][O:4][C:5]([C:7]12[CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH3:23])[CH2:14][CH:13]=[C:12]([I:1])[CH:11]1[CH2:10][N:9]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:8]2)=[O:6]

Participants

5

Reactant 3

HCID 807IodineHCID 8857Ethyl AcetateHCID 86755059HCID 86755059, compound

Product 1

HCID 86755062HCID 86755062, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

106.1 g (0.418 mol) of iodine in 1.1 dm3 of tetrahydrofuran were added dropwise to a solution of 85 g (0.209 mol) of methyl(3aRS,4SR,7aRS)-2-benzyl-7-hydrazono-4-(2-methoxyphenyl)octahydroisoindole-3a-carboxylate in 2 dm3 of tetrahydrofuran. After addition of 2 dm3 of ethyl acetate, the organic phases were washed with two times 1 dm3 of a saturated aqueous sodium hydrogencarbonate solution, washed with two times 1 dm3 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 (95/05 by volume) mixture, 51 g (48%) of methyl(3aRS,4SR,7aRS)-2-benzyl-7-iodo-4-(2-methoxyphenyl)-2,3,3a,4,5,7a-hexahydro-1H-isoindole-3a-carboxylate were obtained in the form of a brown oil, the characteristics of which were as follows:

Workup

  1. washthe organic phases were washed with two times 1 dm3 of a saturated aqueous sodium hydrogencarbonate solution
  2. washwashed with two times 1 dm3 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-0b05d1455ca04f2e9179d97ad5f35caa
Source dataset
uspto-grants-2000_01
Patent number
US06013662

Reaction notes

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