Triethylamine → HCID 22632504, compound

HRID 2417548Notes

Reaction equation

HRID 2417548 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([C:16](OC)=[O:17])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>C(O)C.C1COCC1.[OH-].[Na+].C(OCC)(=O)C>[CH2:1]([N:8]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([CH2:16][OH:17])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 22632373HCID 22632373, compound

Product 1

HCID 22632504HCID 22632504, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

2.04 g (7.8 mmol) of methyl 1-benzyl-4-nitro-1H-pyrazole-3-carboxylate was dissolved in a mixture of 10 ml of ethanol, 10 ml of THF and 5 ml of 1 N sodium hydroxide, and the obtained solution was stirred at room temperature for 4 hours. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the solvent was evaporated, and the obtained crude product was dissolved in 100 ml of THF. 1.5 ml (10.1 mmol) of triethylamine and 0.81 ml (8.5 mmol) of ethyl chloroformate were added to the obtained solution under cooling with ice, and they were stirred at room temperature for 30 minutes. Apiece of ice and 600 mg (15.6 mmol) of sodium borohydride were added to the obtained mixture. The temperature was elevated to room temperature, and the obtained mixture was stirred overnight. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the crude product was obtained. After the purification by the silica gel column chromatography, the title compound was obtained.

Workup

  1. customAfter the treatment with ethyl acetate as the extracting solvent by an ordinary method, the solvent was evaporated
  2. customthe obtained crude product
  3. temperatureunder cooling with ice, and they
  4. stirringwere stirred at room temperature for 30 minutes
  5. customwas elevated to room temperature
  6. stirringthe obtained mixture was stirred overnight
  7. customAfter the purification by the silica gel column chromatography

Sources & evidence

ORD record
ord-8b3d1411c48c4bb4a39dc1d795ec1cd5
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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