Acetic Acid → HCID 22591830, compound

HRID 22899Notes

Reaction equation

HRID 22899 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([N:9]2[C:13](=[O:14])[CH2:12][CH:11]([C:15]([O:17][CH3:18])=[O:16])[CH2:10]2)[CH:6]=[CH:7][CH:8]=1)=O.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1.CC(O)=O>COC(OC)OC>[O:14]=[C:13]1[N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[CH:4]=2)[CH2:10][CH:11]([C:15]([O:17][CH3:18])=[O:16])[CH2:12]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 104392-AminopyridineHCID 131724724HCID 131724724, compound

Product 1

HCID 22591830HCID 22591830, compound

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl (3-formylphenyl)-5-oxopyrrolidine-3-carboxylate, 2-aminopyridine, and AcOH in trimethylorthoformate was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue was re-dissolved in methanol. The solution was then cooled to 0° C. AcOH was added followed by NaBH3CN solid in portions. The reaction was allowed to stirred at room temperature for 8 hours. The reaction solution was then concentrated in vacuo. The residue was dissolved in EtOAc and organic solution was washed with saturated NaHCO3 twice. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel chromatograph (10% meOH/EtOAc) to provide an orange oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was re-dissolved in methanol
  3. additionAcOH was added
  4. concentrationThe reaction solution was then concentrated in vacuo
  5. dissolutionThe residue was dissolved in EtOAc
  6. washorganic solution was washed with saturated NaHCO3 twice
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by silica gel chromatograph (10% meOH/EtOAc)
  10. customto provide an orange oil

Sources & evidence

ORD record
ord-e2bc81ed5ea54e5ab82e0fb636dba177
Source dataset
uspto-grants-2005_02
Patent number
US06849639B2

Reaction notes

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