Potassium Carbonate → (R)-3-(3-Nitro-1h-pyrazol-1-yl)propane-1,2-diol

HRID 18976

Reaction equation

HRID 18976 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 6973630(-)-GlycidolHCID 178526745HCID 178526745, compound

Product 1

HCID 66892928(R)-3-(3-Nitro-1h-pyrazol-1-yl)propane-1,2-diolYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 3-nitro-1H-pyrazole (prepared as in Example 5, 3.00 g, 26.55 mmol) in N,N-dimethylformamide (15 mL) was treated with solid potassium carbonate (5.50 g, 39.82 mmol) and (S)-(−)-glycidol (3.93 g, 53.10 mmol) and placed in a sealed tube and heated at 100° C. for 1 h in an oil bath. After this time the N,N-dimethylformamide was removed in vacuo. Purification by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 12 g; 0% to 10% methanol/dichloromethane) afforded (R)-3-(3-nitro-pyrazol-1-yl)-propane-1,2-diol (3.17 g, 64%) as a yellow oil: LR-ES-MS m/z calculated for C6H9N3O4 [M]+ 187, observed [M+H]+ 188.

Workup

  1. customplaced in a sealed tube
  2. customAfter this time the N,N-dimethylformamide was removed in vacuo
  3. customPurification by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 12 g; 0% to 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-9e35182c67e343e0819f539f6c4280cc
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Linked notes

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