Hydrazine hydrate (1:1) → HCID 68106814, compound

HRID 1809669Notes

Reaction equation

HRID 1809669 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][CH2:8][CH2:9][CH:10]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)[N:11]1C(=O)C2C(=CC=CC=2)C1=O)([CH3:4])([CH3:3])[CH3:2].O.NN>C1COCC1.CO>[C:1]([O:5][C:6](=[O:29])[NH:7][CH2:8][CH2:9][CH:10]([NH2:11])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68107198[3-(3-Chloro-phenyl)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-carbamic acid tert-butyl ester

Product 1

HCID 68106814HCID 68106814, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a stirred solution of [3-(3-chloro-phenyl)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-carbamic acid tert-butyl ester (0.15 g, 0.36 mmol) in THF (2 mL) and methanol (2 mL) was added hydrazine hydrate (0.18 g, 3.6 mmol). The mixture was heated at 55° C. for 2 hours. Then the reaction mixture was concentrated and extracted with ethyl acetate (10 mL). The organic mixture was washed with water (3×1 mL), brine (1 mL), dried over anhydrous sodium sulfate and concentrated to dryness. The residue was purified by column chromatography (methanol:dichloromethane, 1:100) to afford [3-amino-3-(3-chloro-phenyl)-propyl]-carbamic acid tert-butyl ester. (Yield 0.061 g, 60%). LC-MS: [M+H]+ 285.

Workup

  1. concentrationThen the reaction mixture was concentrated
  2. extractionextracted with ethyl acetate (10 mL)
  3. washThe organic mixture was washed with water (3×1 mL), brine (1 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by column chromatography (methanol:dichloromethane, 1:100)

Sources & evidence

ORD record
ord-6eefbfea6f184feabcbda659b1d2ee26
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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