1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-3-nitro-1H-pyrazole → (S)-1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-3-amine

HRID 19192Notes

Reaction equation

HRID 19192 reaction equation
[CH3:1][C:2]1([CH3:16])[O:6][C@@H:5]([CH2:7][N:8]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[N:9]2)[CH2:4][O:3]1.[H][H]>[Pd].C(O)C>[CH3:1][C:2]1([CH3:16])[O:6][C@@H:5]([CH2:7][N:8]2[CH:12]=[CH:11][C:10]([NH2:13])=[N:9]2)[CH2:4][O:3]1

Participants

5

Reactant 2

HCID 593449571-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-3-nitro-1H-pyrazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 57346939(S)-1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-3-amineYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a Parr shaker bottle was placed 1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-3-nitro-1H-pyrazole (700 mg, 3.08 mmol), 10% palladium on carbon (500 mg) and ethanol (25 mL). The bottle was then placed on the Parr shaker at 50 psi of hydrogen pressure for 4 h. The reaction was then filtered through a pad of celite and washed with ethanol and concentrated in vacuo to afford 1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-1H-pyrazol-3-ylamine (550 mg, 91%) as a yellow oil: LR-ES-MS m/z calculated for C9H15N3O2 [M]+ 197, observed 198 [M+H]+.

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-daf74927986e43e59dc354779886f319
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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