Iodine → HCID 86755062, compound

HRID 324669Notes

Reaction equation

HRID 324669 reaction equation
[I:1]I.[CH2:3]([N:10]1[CH2:18][C:17]2([C:19]([O:21][CH3:22])=[O:20])[CH:12]([C:13](=NN)[CH2:14][CH2:15][CH:16]2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH3:30])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(OCC)(=O)C>O1CCCC1>[CH2:3]([N:10]1[CH2:18][C:17]2([C:19]([O:21][CH3:22])=[O:20])[CH:12]([C:13]([I:1])=[CH:14][CH2:15][CH:16]2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH3:30])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

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-9845fe85349e40639fb0b30b345e8492
Source dataset
uspto-grants-2001_04
Patent number
US06218406B1

Reaction notes

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