Acetic Acid → N-(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-1,2,3-triazol-5-amine

HRID 2048513Notes

Reaction equation

HRID 2048513 reaction equation
C([N:8]1[C:12]([NH:13][CH:14]2[CH2:19][CH2:18][CH:17]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH2:16][CH2:15]2)=[CH:11][N:10]=[N:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+].C(O)(=O)C>[C].[Pd].CO>[Si:21]([O:20][CH:17]1[CH2:18][CH2:19][CH:14]([NH:13][C:12]2[NH:8][N:9]=[N:10][CH:11]=2)[CH2:15][CH2:16]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2723923Ammonium formateHCID 670091201-benzyl-N-(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-1,2,3-triazol-5-amine

Product 1

HCID 178455069N-(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-1,2,3-triazol-5-amineYield 65.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-benzyl-N-(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-1,2,3-triazol-5-amine (11.10 g), 10% palladium-carbon (containing water by 50%, 6.66 g), ammonium formate (9.05 g), acetic acid (22 mL) and methanol (220 mL) was stirred at 60° C. for 16 hr under a nitrogen atmosphere. The reaction mixture was filtered, and the solvent was evaporated. 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 basic silica gel chromatography [eluent: hexane/ethyl acetate=70/30→30/70 (volume ratio)] to give the title compound as a colorless oil (5.56 g, 65%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was evaporated
  3. additionThe residue was diluted with saturated aqueous sodium hydrogen carbonate solution
  4. extractionthe mixture was extracted with ethyl acetate-isopropyl alcohol (3:1)
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by basic silica gel chromatography [eluent: hexane/ethyl acetate=70/30→30/70 (volume ratio)]

Sources & evidence

ORD record
ord-a98e47c5f39d462199189af95f169dbf
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

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