Hydrazine hydrate (1:1) → HCID 86755063, compound

HRID 1955420Notes

Reaction equation

HRID 1955420 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][C:14]2([CH3:27])[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.[NH2:30][NH2:31]>CO>[CH2:1]([N:8]1[CH2:16][C:15]2([C:17]([O:19][CH3:20])=[O:18])[CH:10]([C:11](=[N:30][NH2:31])[CH2:12][CH2:13][C:14]2([CH3:27])[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 86755064HCID 86755064, compound

Product 1

HCID 86755063HCID 86755063, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3 g (7.95 mmol) of methyl (3aRS,4SR,7aRS)-2-benzyl-4-methyl-7-oxo-4-phenyloctahydroisoindole-3a-carboxylate and of 1.55 cm3 (31.8 mmol) of hydrazine hydrate in 30 cm3 of methanol was brought to reflux for two hours. After concentrating the methanol under reduced pressure, the residue was taken up in dichloromethane, washed with three times 30 cm3 of distilled water, dried over magnesium sulphate and concentrated under reduced pressure. 2.8 g (89%) of methyl (3aRS,4SR,7aRS)-2-benzyl-7-hydrazono-4-methyl-4-phenyloctahydroisoindole-3a-carboxylate were thus obtained in the form of a brown oil, the characteristics of which were as follows:

Workup

  1. temperatureto reflux for two hours
  2. concentrationAfter concentrating the methanol under reduced pressure
  3. washwashed with three times 30 cm3 of distilled water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-477c1f8143eb43f3960f3d85e4cbe629
Source dataset
uspto-grants-2000_09
Patent number
US06124465

Reaction notes

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