HCID 19814286, compound → HCID 19814358, compound

HRID 466613Notes

Reaction equation

HRID 466613 reaction equation
[CH2:1]([N:8]1[CH2:23][CH2:22][C:11]2([O:15][C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH3:19])[C:12]2(O)[CH3:20])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.C(OC(=O)C)(=O)C>[CH2:1]([N:8]1[CH2:23][CH2:22][C:11]2([O:15][C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH3:19])[C:12]2=[CH2:20])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 19814286HCID 19814286, compound

Product 1

HCID 19814358HCID 19814358, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

After refluxing a solution containing 9.6 g of 8-benzyl-4-hydroxy-4-methyl-2-oxo-3-propyl-1-oxa-3,8-diazaspiro[4,5]decane in a mixture of 96 ml of acetic acid and 5.7 ml of acetic anhydride under argon for 5 hours the solvent is evaporated under reduced pressure. After adding 5% by weight aqueous sodium hydroxide solution to the residue up to a pH value of 10, the mixture is extracted with benzene and the organic phase is washed to neutral with water. After drying the organic phase over anhydrous sodium sulfate benzene is evaporated under reduced pressure. After recrystallizing the residue from diisopropyl ether the title compound is obtained in 86.4% yield, m.p.: 70°-71° C.

Workup

  1. temperatureAfter refluxing a solution
  2. customis evaporated under reduced pressure
  3. additionAfter adding 5% by weight aqueous sodium hydroxide solution to the residue up to a pH value of 10
  4. extractionthe mixture is extracted with benzene
  5. washthe organic phase is washed to neutral with water
  6. dry with materialAfter drying the organic phase over anhydrous sodium sulfate benzene
  7. customis evaporated under reduced pressure
  8. customAfter recrystallizing the residue from diisopropyl ether the title compound
  9. customis obtained in 86.4% yield, m.p.: 70°-71° C.

Sources & evidence

ORD record
ord-c4f8c7b93e0241e480c4feaa6d0a4ba2
Source dataset
uspto-grants-1992_10
Patent number
US05157038

Reaction notes

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