Water → HCID 178434101, compound

HRID 1688483Notes

Reaction equation

HRID 1688483 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:15][C:16]1[NH:17][C:18]([NH2:21])=[N:19][N:20]=1.[CH2:22]1[O:32][C:25]2([CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]2)[O:24][CH2:23]1.O>C(O)(=O)C>[O:24]1[C:25]2([CH2:30][CH2:29][CH:28]([NH:21][C:18]3[NH:17][C:16]([CH3:15])=[N:20][N:19]=3)[CH2:27][CH2:26]2)[O:32][CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5049666Sodium triacetoxyborohydrideHCID 178434112HCID 178434112, compound

Product 1

HCID 178434101HCID 178434101, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium triacetoxyborohydride (32.4 g) was gradually added to a solution (150 mL) of 5-methyl-4H-1,2,4-triazol-3-amine (10.0 g) and 1,4-cyclohexanedione monoethyleneketal (19.1 g) in acetic acid. The mixture was stirred at room temperature for 16 hr, water 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, and the mixture was extracted 3 times 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, and the residue was solidified with diisopropyl ether, and the solid was collected by filtration, and dried to give the title compound (15.6 g).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionThe obtained residue was poured into saturated aqueous sodium hydrogen carbonate
  3. extractionthe mixture was extracted 3 times 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. filtrationthe solid was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-14c55b383be74dbeb1422da805168b19
Source dataset
uspto-grants-2012_04
Patent number
US08148383B2

Reaction notes

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