(S)-3-(4-Nitro-pyrazol-1-yl)-propane-1,2-diol → (S)-3-(4-Amino-pyrazol-1-yl)-propane-1,2-diol

HRID 55874Notes

Reaction equation

HRID 55874 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][C@H:10]([OH:13])[CH2:11][OH:12])[CH:8]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[N:6][N:7]([CH2:9][C@H:10]([OH:13])[CH2:11][OH:12])[CH:8]=1

Participants

4

Reactant 1

HCID 12151831(S)-3-(4-Nitro-pyrazol-1-yl)-propane-1,2-diol

Product 1

HCID 67127782(S)-3-(4-Amino-pyrazol-1-yl)-propane-1,2-diol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

(S)-3-(4-Nitro-pyrazol-1-yl)-propane-1,2-diol (29) (180 mg, 10 mmol), and 10% Pd/C (116 mg) in methanol (20 mL) were stirred under hydrogen for at atmospheric pressure and room temperature for 48 h. The reaction mixture was subsequently filtered through celite and concentrated to give A3-2 (160 mg, 100%); LCMS, Rt=0.28 min (MeOH-FA method), m/z 158 (MH+).

Workup

  1. filtrationThe reaction mixture was subsequently filtered through celite and
  2. concentrationconcentrated
  3. customto give A3-2 (160 mg, 100%)

Sources & evidence

ORD record
ord-758575b725174cea982b4e0c359520ae
Source dataset
uspto-grants-2016_09
Patent number
US09433622B2

Reaction notes

Loading…