Hydrazine hydrate (1:1) → Tert-butyl (2-amino-2-(3-chlorophenyl)ethyl)carbamate

HRID 1186547Notes

Reaction equation

HRID 1186547 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][CH:9]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1)[N:10]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:28])[NH:7][CH2:8][CH:9]([NH2:10])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68106925HCID 68106925, compound

Product 1

HCID 69108731Tert-butyl (2-amino-2-(3-chlorophenyl)ethyl)carbamate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a stirred solution of [2-(3-chloro-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethy]-carbamic acid tert-butyl ester (2.5 g, 6.2 mmol) in THF (10 mL) and methanol (10 mL) was added hydrazine hydrate (3.1 g, 62 mmol). The mixture was heated a 55° C. for 1 hour. Then it was concentrated to dryness, dissolved in H2O (5 mL) and extracted with ethyl acetate (50 mL). The organic mixture was concentrated and purified by column chromatography (methanol:dichloromethane, 1:100) to afford [2-amino-2-(3-chloro-phenyl)-ethyl]-carbamic acid tert-butyl ester. (Yield 1.325 g, 79%). LC-MS: [M+H]+ 271.

Workup

  1. concentrationThen it was concentrated to dryness
  2. dissolutiondissolved in H2O (5 mL)
  3. extractionextracted with ethyl acetate (50 mL)
  4. concentrationThe organic mixture was concentrated
  5. custompurified by column chromatography (methanol:dichloromethane, 1:100)

Sources & evidence

ORD record
ord-48374491a50844928927f432a8c535f4
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

Loading…