Water → HCID 178455070, compound

HRID 519587Notes

Reaction equation

HRID 519587 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([NH2:6])=[N:2]1.[Si:7]([O:14][CH:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].C([BH3-])#N.[Na+].O>C(O)(=O)C>[Si:7]([O:14][CH:15]1[CH2:16][CH2:17][CH:18]([NH:6][C:3]2[NH:4][CH:5]=[N:1][N:2]=2)[CH2:19][CH2:20]1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 106094304-(tert-Butyldimethylsilyloxy)cyclohexanoneHCID 178418311HCID 178418311, compound

Product 1

HCID 178455070HCID 178455070, compoundYield 20.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution (30 mL) of 1H-1,2,4-triazol-3-amine (3 g) and 4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexanone (10 g) in acetic acid was added sodium cyanoborohydride (9.3 g), and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the solvent was evaporated under reduced pressure. The obtained residue was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1). The obtained extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless solid (2.2 g, 20%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionThe obtained residue was poured into saturated aqueous sodium hydrogen carbonate
  3. extractionthe mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1)
  4. extractionThe obtained extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-318f3816bd324739ad380af490178a5f
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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