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

HRID 1366513Notes

Reaction equation

HRID 1366513 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 108%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(phenylmethyl)-5-azaspiro[2.4]heptane-4,7-dione (2.7802 g, 12.92 mmol) in MeOH (65 mL) was added sodium acetate (2.12 g, 25.8 mmol) and O-methylhydroxylamine hydrochloride (2.16 g, 25.9 mmol). The mixture was stirred overnight, and then diluted with DCM (100 mL). The mixture was washed with sat. aq. NaHCO3, and the organic phase was dried over anhydrous MgSO4, filtered, and concentrated in vacuo to give crude (7Z)-5-(phenylmethyl)-5-azaspiro[2.4]heptane-4,7-dione 7-(O-methyloxime) (3.4094 g, >100% crude yield) as a yellow oil. LCMS: (M+H)+: 245.1.

Workup

  1. washThe mixture was washed with sat. aq. NaHCO3
  2. dry with materialthe organic phase was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-741725e2872840aa920a555348338243
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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