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 2381283Notes

Reaction equation

HRID 2381283 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]>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

5

Reactant 2

HCID 593449371-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-3-nitro-1H-pyrazoleHCID 178418361HCID 178418361, compound

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-ylmethyl)-3-nitro-1H-pyrazole (14.5 g) in ethanol (60 mL) was treated with 10% palladium on activated carbon (1.4 g). The mixture was placed on a Parr shaker and exposed to hydrogen (50 psi) for 16 h. After this time, the mixture was filtered through diatomaceous earth. The filtrate was concentrated in vacuo to afford 1-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrazol-3-ylamine (12.4 g, 98%) as an amorphous yellow oil; ESI-LRMS m/e calcd for C9H15N3O2 [M+H+] 198, found 198 [M+H+]. 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. filtrationAfter this time, the mixture was filtered through diatomaceous earth
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8a30359752c440188e20ac1d302cee72
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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