Water → N-(1,4-dioxaspiro[4.5]dec-8-yl)-4H-1,2,4-triazol-3-amine

HRID 519528Notes

Reaction equation

HRID 519528 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([NH2:6])=[N:2]1.[O:7]1[C:11]2([CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>C(O)(=O)C>[O:7]1[C:11]2([CH2:16][CH2:15][CH:14]([NH:6][C:3]3[NH:4][CH:5]=[N:1][N:2]=3)[CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5049666Sodium triacetoxyborohydrideHCID 178418311HCID 178418311, compound

Product 1

HCID 178420920N-(1,4-dioxaspiro[4.5]dec-8-yl)-4H-1,2,4-triazol-3-amineYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1H-1,2,4-triazol-3-amine (66.6 g) and 1,4-dioxaspiro[4.5]decan-8-one (175 g) in acetic acid (1.25 L) was gradually added sodium triacetoxyborohydride (252 g) under ice-cooling. After stirring at room temperature for 16 hr, water (1 L) was added to the reaction mixture, and the mixture was concentrated under reduced pressure. The obtained residue was poured into saturated aqueous sodium hydrogen carbonate (1 L). The mixture was neutralized with sodium bicarbonate, and extracted 3 times with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1, 2 L). The combined extracts were dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was solidified with diisopropyl ether (500 mL), and the resulting solid was collected by filtration, washed twice with diisopropyl ether (250 mL), and dried to give the title compound (166 g, 94%).

Workup

  1. temperaturecooling
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionThe obtained residue was poured into saturated aqueous sodium hydrogen carbonate (1 L)
  4. extractionextracted 3 times with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1, 2 L)
  5. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. filtrationthe resulting solid was collected by filtration
  8. washwashed twice with diisopropyl ether (250 mL)
  9. customdried

Sources & evidence

ORD record
ord-1bec0273a5f14a85a1aafe281a16de96
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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