Sodium triacetoxyborohydride → HCID 178469196, compound

HRID 2048521Notes

Reaction equation

HRID 2048521 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([NH2:7])=[N:5][N:6]=1.O=[C:9]1[CH2:12][CH:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:10]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[CH3:1][C:2]1[NH:3][C:4]([NH:7][CH:9]2[CH2:12][CH:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:10]2)=[N:5][N:6]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 22467070Ethyl 3-oxocyclobutanecarboxylateHCID 178434112HCID 178434112, compound

Product 1

HCID 178469196HCID 178469196, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-methyl-4H-1,2,4-triazol-3-amine (16.35 g) and ethyl 3-oxocyclobutanecarboxylate (12.41 g) in acetic acid (150 mL) was added sodium triacetoxyborohydride (36.56 g), and the mixture was stirred at room temperature for 5 days. The solvent was evaporated under reduced pressure, the residue was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate-isopropyl alcohol (3:1). The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography [eluent: methanol/ethyl acetate=0/100→10/90 (volume ratio)], and crystallized from diethyl ether to give the title compound as a colorless solid (15.93 g, 62%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with saturated aqueous sodium hydrogen carbonate solution
  3. extractionthe mixture was extracted with ethyl acetate-isopropyl alcohol (3:1)
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel chromatography [eluent: methanol/ethyl acetate=0/100→10/90 (volume ratio)]
  8. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-9a99e3ba49e0499f8d303083ed63e24a
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

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