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

HRID 18985Notes

Reaction equation

HRID 18985 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>C(O)C.[Pd]>[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

4

Reactant 1

HCID 593449371-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-3-nitro-1H-pyrazole

Product 1

HCID 59344941(R)-1-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-3-amineYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl-methyl)-3-nitro-1H-pyrazole (14.5 g, 63.8 mmol) was diluted in 60 mL of ethanol and 10% palladium on carbon (1.4 g) was added. The mixture was hydrogenated on a Parr apparatus at 50 psi for 16 h. The mixture was filtered and the solvent was removed to afford the product 1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-1H-pyrazol-3-ylamine (12.4 g, 98%) as a pale yellow oil. LR-ES-MS m/z calculated for C9H15N3O2 [M]+ 197, observed [M+H]+ 198. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.24 (s, 3H), 1.30 (s, 3H), 3.70 (dd, J=8.5, 6.0 Hz, 1H), 3.85-4.02 (m, 3H), 4.28 (quin, J=6.0 Hz, 1H), 4.56 (s, 2H), 5.36 (d, J=2.1 Hz, 1H), 7.30 (d, J=2.1 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-b5de005694114002ab6705c245678fa7
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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