Potassium Carbonate → (S)-3-(3-nitro-1h-pyrazol-1-yl)propane-1,2-diol

HRID 19190Notes

Reaction equation

HRID 19190 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:15]1[O:17][C@@H:16]1[CH2:18][OH:19]>CN(C)C=O>[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:15][C@H:16]([OH:17])[CH2:18][OH:19])[N:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5460455(+)-GlycidolHCID 178526745HCID 178526745, compound

Product 1

HCID 59344949(S)-3-(3-nitro-1h-pyrazol-1-yl)propane-1,2-diolYield 30.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 3-nitro-1H-pyrazole (prepared as in Example 5, 2.00 g, 17.70 mmol) in N,N-dimethylformamide (20 mL) was treated with potassium carbonate (3.66 g, 26.55 mmol) and (R)-glycidol (2.62 g, 35.40 mmol). The reaction mixture was stirred for 2 h at 100° C. under nitrogen. Upon completion of the reaction the N,N-dimethylformamide was removed under reduced pressure and the crude product obtained was purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% to 10% methanol/dichloromethane) to afford (S)-3-(3-nitro-pyrazol-1-yl)propane-1,2-diol (1.00 g, 30%) as a yellow oil: LR-ES-MS m/z calculated for C6H9N3O4 [M]+ 187, observed 188 [M+H]+.

Workup

  1. customwas removed under reduced pressure
  2. customthe crude product obtained
  3. customwas purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% to 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-f8b4d39a9a464986bbe12bff7e8463f1
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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