Tert-butyl 2-(4-nitro-1H-imidazol-1-YL)ethylcarbamate → Tert-butyl 2-(4-amino-1H-imidazol-1-YL)ethylcarbamate

HRID 1818933Notes

Reaction equation

HRID 1818933 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([N+:15]([O-])=O)[N:12]=[CH:11]1)([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([NH2:15])[N:12]=[CH:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 10422534Tert-butyl 2-(4-nitro-1H-imidazol-1-YL)ethylcarbamate

Product 1

HCID 68425567Tert-butyl 2-(4-amino-1H-imidazol-1-YL)ethylcarbamateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A flask containing compound 39.2 (400 mg, 1.56 mmol) and 10% (dry basis) palladium on activated carbon (−50% wet, Deguessa, 664 mg, ˜0.312 mmol) in MeOH (6.0 mL) was sealed with a septum and purged with nitrogen followed by hydrogen. The mixture was stirred under hydrogen (balloon pressure) at ambient temperature for 3 hours. After completion of the reaction, the mixture was filtered through a plug of celite and concentrated. The residue was dried under high-vacuum to yield 353 mg (quantitative) of [2-(4-amino-imidazol-1-yl)-ethyl]-carbamic acid tert-butyl ester (compound 39.3) as a solid, ES (+) MS m/e=227 (M+H+).

Workup

  1. customwas sealed with a septum
  2. custompurged with nitrogen
  3. customAfter completion of the reaction
  4. filtrationthe mixture was filtered through a plug of celite
  5. concentrationconcentrated
  6. customThe residue was dried under high-vacuum

Sources & evidence

ORD record
ord-356f829604b44ff39f8e77ee444b02cd
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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