(3-Nitro-pyrazol-1-yl)-propionic acid tert-butyl ester → (3-Amino-pyrazol-1-yl)-propionic acid tert-butyl ester

HRID 545997Notes

Reaction equation

HRID 545997 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH:7]([N:9]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[N:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6](=[O:17])[CH:7]([N:9]1[CH:13]=[CH:12][C:11]([NH2:14])=[N:10]1)[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 65814351(3-Nitro-pyrazol-1-yl)-propionic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 67190546(3-Amino-pyrazol-1-yl)-propionic acid tert-butyl esterYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23938PalladiumSolvent

Conditions

Temperature
25 °C

Procedure

To a solution containing (3-nitro-pyrazol-1-yl)-propionic acid tert-butyl ester (2.30 g, 9.53 mmol) in methanol (100 mL), palladium, 10 wt. % on activated carbon, wet (˜300 mg) was added to the solution. The vial was charged with hydrogen gas (via balloon) and the mixture was stirred for 16 h at 25° C. The mixture was passed through a plug of celite and concentrated in vacuo to afford (3-amino-pyrazol-1-yl)-propionic acid tert-butyl ester (1.87 g, 93%) as a yellow oil which was used in the following step with no further purification.

Workup

  1. additionwas added to the solution
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a2df2c42e7e4f48b3e06c3733c4d989
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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