Ethyl Acetate → 5-Cyano-2,4-dioxo-3-azaspiro[5,5]undecane-1-carboxylic acid

HRID 130578Notes

Reaction equation

HRID 130578 reaction equation
[C:1]([CH:3]1[C:8]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7]([C:14]([O:16]CC2C=CC=CC=2)=[O:15])[C:6](=[O:24])[NH:5][C:4]1=[O:25])#[N:2].C(OCC)(=O)C>[Pd].CO>[C:1]([CH:3]1[C:8]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7]([C:14]([OH:16])=[O:15])[C:6](=[O:24])[NH:5][C:4]1=[O:25])#[N:2]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 11233094Benzyl 5-cyano-2,4-dioxo-3-azaspiro[5,5]undecane-1-carboxylate

Product 1

HCID 111493685-Cyano-2,4-dioxo-3-azaspiro[5,5]undecane-1-carboxylic acidYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
12 °C

Procedure

1.8 g of benzyl 5-cyano-2,4-dioxo-3-azaspiro[5,5]undecane-1-carboxylate, 25 ml of ethyl acetate and 0.09 g of 5% Pd/C are placed in a 100 ml flask equipped with a magnetic stirrer, thermometer and condenser. The mixture is stirred for 4 hours at 12° C. under a hydrogen atmosphere. 10 ml methanol are added and the mixture is filtered through celite. The solvent is evaporated at 20° C. under reduced pressure to obtain 1.32 g of 5-cyano-2,4-dioxo-3-azaspiro[5,5]undecane-1-carboxylic acid.

Workup

  1. customequipped with a magnetic stirrer
  2. filtrationthe mixture is filtered through celite
  3. customThe solvent is evaporated at 20° C. under reduced pressure

Sources & evidence

ORD record
ord-d16334f49c0a4770b0e2ff5dc1979eff
Source dataset
uspto-grants-2008_06
Patent number
US07381823B2

Reaction notes

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