Hydrazine hydrate (1:1) → [2-(2-Amino-ethyl)-phenyl]-acetic acid tert-butyl ester

HRID 890823Notes

Reaction equation

HRID 890823 reaction equation
[C:1]([O:5][C:6](=[O:27])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]=[CH:15][N:16]1C(=O)C2C(=CC=CC=2)C1=O)([CH3:4])([CH3:3])[CH3:2].O.NN>CCO>[C:1]([O:5][C:6](=[O:27])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][NH2:16])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 53900851HCID 53900851, compound

Product 1

HCID 54411372[2-(2-Amino-ethyl)-phenyl]-acetic acid tert-butyl esterYield 66.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of {2-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-vinyl]-phenyl}-acetic acid tert-butyl ester (1.97 g) and hydrazine hydrate (1.97 mL) in EtOH (75 mL) was heated at reflux for 90 minutes. The solids were removed by filtration and the filtrate was concentrated in vacuo. The residue was dissolved in EtOAc (50 mL) and the solution was washed with saturated NaHCO3 followed by brine. The organic solution was dried over MgSO4, filtered, and concentrated. Purification by flash chromatography (CHCl3:MeOH 97.5:2.5 to 95:5 to 9:1) provided the title amine (853 mg). MS 236 (M+1).

Workup

  1. temperatureat reflux for 90 minutes
  2. customThe solids were removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc (50 mL)
  5. washthe solution was washed with saturated NaHCO3
  6. dry with materialThe organic solution was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash chromatography (CHCl3:MeOH 97.5:2.5 to 95:5 to 9:1)

Sources & evidence

ORD record
ord-e392063998654e1c8aaded963197c419
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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