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

HRID 55873

Reaction equation

HRID 55873 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[CH2:9]1[O:11][C@H:10]1[CH2:12][OH:13].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][C@H:10]([OH:11])[CH2:12][OH:13])[CH:8]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 163764-nitro-1H-pyrazoleHCID 6973630(-)-Glycidol

Product 1

HCID 12151831(S)-3-(4-Nitro-pyrazol-1-yl)-propane-1,2-diolYield 18.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Nitro-1-H-pyrazole (27) (600 mg, 5.3 mmol), (S)-glycidol (702 μL, 10.6 mmol) and K2CO3 (1.1 g, 8.0 mmol) in acetonitrile (7 mL) were heated in the microwave at 100° C. for 1 h. The solvent was evaporated in vacuo and the residue dissolved in ethyl acetate (20 mL) and water (20 mL). The organic layer was separated and the aqueous layer further extracted with ethyl acetate (10×20 mL). The organics were combined, dried over MgSO4, filtered and evaporated to give a crude oil. This was purified by flash chromatography on silica eluting with a gradient of 70% ethyl acetate/isohexane to ethyl acetate, to give the desired compound as a white solid (180 mg, 18%); LCMS, Rt=0.98 min (MeOH-FA method), m/z 188 (MH+).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate (20 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer further extracted with ethyl acetate (10×20 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give a crude oil
  9. customThis was purified by flash chromatography on silica eluting with a gradient of 70% ethyl acetate/isohexane to ethyl acetate

Sources & evidence

ORD record
ord-68beedd3b869405c8a09aa982d7b606e
Source dataset
uspto-grants-2016_09
Patent number
US09433622B2

Linked notes

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