Hydrazine hydrate (1:1) → HCID 86757101, compound

HRID 1383731Notes

Reaction equation

HRID 1383731 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][CH:8]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:23]=1)[CH2:9][N:10]1C(=O)C2C(=CC=CC=2)C1=O)([CH3:4])([CH3:3])[CH3:2].O.NN>CO>[C:1]([O:5][C:6](=[O:33])[NH:7][CH:8]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:23]=1)[CH2:9][NH2:10])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86757102HCID 86757102, compound

Product 1

HCID 86757101HCID 86757101, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution in methanol (15 ml) of the mixture containing [1-[(3-tert-butyl-4-hydroxyphenyl)methyl)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)ethyl]carbamic acid tert-butyl ester, hydrazine monohydrate (2 ml) was added and the resulting mixture was stirred at room temperature for 4 hours. After filtering, the filtrate was concentrated under reduced pressure and the resulting residue was subjected to silica gel column chromatography (eluting solvent consisting of chloroform, methanol and aqueous ammonia at a ratio of 10:1:0.1) to give [2-amino-1-[(3-tert-butyl-4-hydroxyphenyl)methyl]ethyl]carbamic acid tert-butyl ester in the amount of 1.55 g (69%).

Workup

  1. additionwas added
  2. filtrationAfter filtering
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washeluting solvent

Sources & evidence

ORD record
ord-0b274240e59f495cb8cd0b4c2dc6e877
Source dataset
uspto-grants-2001_07
Patent number
US06255285B1

Reaction notes

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