tert-butyl 3-(4-nitro-1H-pyrazol-1-yl)azetidine-1-carboxylate → 4-Amino-1-(1-Boc-azetidin-3-yl)-1H-pyrazole

HRID 714846Notes

Reaction equation

HRID 714846 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH:9]2[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]2)[CH:8]=1)([O-])=O>C(O)C.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[N:6][N:7]([CH:9]2[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]2)[CH:8]=1

Participants

4

Reactant 1

HCID 56777239tert-butyl 3-(4-nitro-1H-pyrazol-1-yl)azetidine-1-carboxylate

Product 1

HCID 272815264-Amino-1-(1-Boc-azetidin-3-yl)-1H-pyrazoleYield 44.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 3-(4-nitro-1H-pyrazol-1-yl)azetidine-1-carboxylate (5.3 g) obtained in Step B of Example 131 in ethanol (30 mL) was added 5% palladium-carbon (4.2 g), and the mixture was stirred at room temperature for 2 hr under hydrogen atmosphere (at normal pressures). The palladium-carbon was removed by filtration through Celite, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (2.1 g).

Workup

  1. customThe palladium-carbon was removed by filtration through Celite
  2. customthe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5596432afa3d40f09660874bca3a7404
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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