Water → HCID 57964979, compound

HRID 1931579Notes

Reaction equation

HRID 1931579 reaction equation
[CH:1]([C:4]1[N:8]=[C:7]([CH:9]2[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]2)[O:6][N:5]=1)([CH3:3])[CH3:2].O.[NH2:17][NH2:18].[BH4-].[Na+].O>CO>[CH:1]([C:4]1[N:8]=[C:7]([CH:9]2[CH2:14][CH2:13][CH:12]([NH:17][NH2:18])[CH2:11][CH2:10]2)[O:6][N:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 4311764Sodium borohydrideHCID 579649554-(3-Isopropyl-1,2,4-oxadiazol-5-YL)cyclohexan-1-one2×

Product 1

HCID 57964979HCID 57964979, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-cyclohexanone (Intermediate 11; 600 mg, 2.9 mmol) and hydrazine hydrate (160 mg, 3.2 mmol) in methanol (2 mL) was heated at reflux for 3 h. The reaction mixture was cooled to 0° C. and sodium borohydride (220 mg, 5.8 mmol) was added portionwise. The reaction mixture was stirred at 0° C. for 4 h and then at room temperature overnight. Water was added and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were dried (sodium sulfate), filtered, and evaporated to give [4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-cyclohexyl]-hydrazine (280 mg, 43%) which was used directly in the next step without further purification. Mass spectrum M+=224.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. customat room temperature
  4. customovernight
  5. extractionthe aqueous layer was extracted three times with ethyl acetate
  6. dry with materialThe combined organic layers were dried (sodium sulfate)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-d534982253bc416bbdbdea12a5bd85f7
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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