Hydrazine hydrate (1:1) → HCID 86757406, compound

HRID 1596756Notes

Reaction equation

HRID 1596756 reaction equation
[CH2:1]([N:8]1[CH2:16][C:15]2([C:17]([O:19][CH3:20])=[O:18])[CH:10]([C:11](=O)[CH2:12][CH2:13][CH:14]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:29][NH2:30]>C(O)C>[CH2:1]([N:8]1[CH2:16][C:15]2([C:17]([O:19][CH3:20])=[O:18])[CH:10]([C:11](=[N:29][NH2:30])[CH2:12][CH2:13][CH:14]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 11302988methyl(3aRS,4SR,7aRS)-2-benzyl-7-oxo-4-phenyloctahydroisoindole-3a-carboxylate

Product 1

HCID 86757406HCID 86757406, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 100 g (0.275 mol) of the levorotatory enantiomer of methyl (3aRS,4RS,7aSR)-2-benzyl-4-phenyl-7-oxoperhydroisoindole-3a-carboxylate and of 50 g (1 mol) of hydrazine hydrate in 750 cm3 of ethanol is brought to reflux for one and a half hours. After concentrating the ethanol under reduced pressure, the residue is taken up in 400 cm3 of dichloromethane and the organic phase is washed with distilled water and then with a saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. 100 g (960%) of the levorotatory enantiomer of methyl (3aRS,4SR,7aRS)-2-benzyl-7-hydrazono-4-phenylperhydroisoindole-3a-carboxylate are thus obtained in the form of a yellow oil used as is in the following stage.

Workup

  1. temperatureto reflux for one and a half hours
  2. concentrationAfter concentrating the ethanol under reduced pressure
  3. washthe organic phase is washed with distilled water
  4. dry with materialwith a saturated aqueous sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-96ce0a1a56174f96b5067abbb0d893d4
Source dataset
uspto-grants-2001_09
Patent number
US06291679B1

Reaction notes

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