(S)-1-(5-methyl-4-nitro-1H-pyrazol-1-yl)propan-2-ol → (S)-1-(4-amino-5-methyl-1H-pyrazol-1-yl)propan-2-ol

HRID 522691Notes

Reaction equation

HRID 522691 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C@@H:8]([OH:10])[CH3:9])[N:5]=[CH:4][C:3]=1[N+:11]([O-])=O>CO.[Pd]>[NH2:11][C:3]1[CH:4]=[N:5][N:6]([CH2:7][C@@H:8]([OH:10])[CH3:9])[C:2]=1[CH3:1]

Participants

4

Reactant 1

HCID 118023522(S)-1-(5-methyl-4-nitro-1H-pyrazol-1-yl)propan-2-ol

Product 1

HCID 118022491(S)-1-(4-amino-5-methyl-1H-pyrazol-1-yl)propan-2-olYield 114.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-1-(5-methyl-4-nitro-1H-pyrazol-1-yl)propan-2-ol (100 mg, 0.54 mmol) in methanol (20 mL) was added 10% Pd/C (20 mg). The reaction mixture was stirred under 1 atm H2 atmosphere at room temperature overnight, and filtered through a pad of Celite. The filtrate was concentrated to give (S)-1-(4-amino-5-methyl-1H-pyrazol-1-yl)propan-2-ol (96 mg, crude) as a yellowish oil. MS (ES+) C7H13N3O requires: 155, found: 156 [M+H]+.

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-65d464bccaed4408aff3a9b9867c892f
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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