Sodium → 7,9-Dioxo-6-aza-spiro[3.5]nonane-8-carboxylic acid methyl ester

HRID 1175168Notes

Reaction equation

HRID 1175168 reaction equation
C(O[C:4]([C:6]1([CH2:10][NH:11][C:12](=[O:18])[CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH2:9][CH2:8][CH2:7]1)=[O:5])C.[Na]>C1(C)C=CC=CC=1.CO>[CH3:17][O:16][C:14]([CH:13]1[C:4](=[O:5])[C:6]2([CH2:7][CH2:8][CH2:9]2)[CH2:10][NH:11][C:12]1=[O:18])=[O:15]

Participants

5

Reactant 2

HCID 5360545SodiumHCID 57654660HCID 57654660, compound

Product 1

HCID 595585517,9-Dioxo-6-aza-spiro[3.5]nonane-8-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

1-[(2-Methoxycarbonyl-acetylamino)-methyl]-cyclobutanecarboxylic acid ethyl ester (1.62 g, 6.3 mmol) dissolved in 15 ml toluene is added dropwise to a freshly prepared solution of sodium (0.15 g, 6.5 mmol) in methanol (20 ml). The reaction mixture is refluxed for 3 hours and then extracted 3 times with water. The aqueous phase is acidified using HClconc. and the now acidic solution is extracted with ethyl acetate. Drying and evaporation of the solvent delivered the crude product which is used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture is refluxed for 3 hours
  2. extractionextracted 3 times with water
  3. extractionand the now acidic solution is extracted with ethyl acetate
  4. customDrying
  5. customevaporation of the solvent
  6. customis used in the next step without further purification

Sources & evidence

ORD record
ord-b82e4be28bce4a3585011ce0074a7585
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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