Sodium Acetate → (7Z)-5-benzyl-7-methoxyimino-5-azaspiro[2.4]heptan-4-one

HRID 1366525Notes

Reaction equation

HRID 1366525 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:14][C:13](=O)[C:10]3([CH2:12][CH2:11]3)[C:9]2=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[Na+].Cl.[CH3:23][O:24][NH2:25]>CO.C(Cl)Cl>[CH3:23][O:24]/[N:25]=[C:13]1\[CH2:14][N:8]([CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:9](=[O:16])[C:10]2\1[CH2:12][CH2:11]2

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 98777875-Benzyl-5-azaspiro[2.4]heptane-4,7-dione

Product 1

HCID 87210371(7Z)-5-benzyl-7-methoxyimino-5-azaspiro[2.4]heptan-4-oneYield 95.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

5-(Phenylmethyl)-5-azaspiro[2.4]heptane-4,7-dione (Example 128) (2.8619 g, 13.29 mmol), sodium acetate (2.23 g, 26.59 mmol), and O-methylhydroxylamine hydrochloride (2.22 g, 26.59) was dissolved in 65 mL of MeOH. The mixture was stirred at room temperature overnight and then diluted with 300 mL of DCM. The mixture was washed with sat. aq. NaHCO3 (200 mL), and the organics were dried over anhydrous MgSO4, filtered, and concentrated in vacuo to provide (7Z)-5-(phenylmethyl)-5-azaspiro[2.4]heptane-4,7-dione 7-(O-methyloxime) (3.0864 g, 95%). LCMS: (M+H)+: 245.1.

Workup

  1. washThe mixture was washed with sat. aq. NaHCO3 (200 mL)
  2. dry with materialthe organics were dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-81331d3e6725452586a1c21b19ec799b
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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