(R)-3-(3-Nitro-1h-pyrazol-1-yl)propane-1,2-diol → (R)-3-(3-amino-pyrazol-1-yl)-propane-1,2-diol

HRID 18977Notes

Reaction equation

HRID 18977 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:9][C@@H:10]([OH:13])[CH2:11][OH:12])[N:5]=1)([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:8]=[CH:7][N:6]([CH2:9][C@@H:10]([OH:13])[CH2:11][OH:12])[N:5]=1

Participants

5

Reactant 2

HCID 66892928(R)-3-(3-Nitro-1h-pyrazol-1-yl)propane-1,2-diolHCID 178418361HCID 178418361, compound

Product 1

HCID 66894729(R)-3-(3-amino-pyrazol-1-yl)-propane-1,2-diolYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a Parr shaker bottle was placed (R)-3-(3-nitro-pyrazol-1-yl)-propane-1,2-diol (3.17 g, 16.95 mmol), 10% palladium on activated carbon (200 mg) and ethanol (30 mL). The bottle was then placed on the Parr shaker at 50 psi of hydrogen pressure for 5 h. The reaction was then filtered through a pad of celite and washed with ethanol and concentrated in vacuo to afford (R)-3-(3-amino-pyrazol-1-yl)-propane-1,2-diol (2.60 g, 98%) as a yellow oil: LR-ES-MS m/z calculated for C6H11N3O2 [M]+ 157, observed [M+H]+ 158.

Workup

  1. filtrationThe reaction was then filtered through a pad of celite
  2. washwashed with ethanol
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1656d1b5f0744c86a70eff34bdd81332
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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