Tert-butyl 3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate → 1,1-Dimethylethyl 3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate

HRID 245913Notes

Reaction equation

HRID 245913 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:13](=[O:14])[CH:12]2[CH2:15][CH:9]1[CH:10]=[CH:11]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:13](=[O:14])[CH:12]2[CH2:15][CH:9]1[CH2:10][CH2:11]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 15319948Tert-butyl 3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 224086881,1-Dimethylethyl 3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylateYield 105.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a Parr pressure bottle, 3-oxo-2-aza-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid tert-butyl ester (1.77 g, 8.46 mmol) was dissolved in methanol (12 ml) and 10% palladium on carbon (wet, 170 mg, 0.16 mmol) was carefully added. The bottle was placed on a Parr hydrogenator and shaken under 40 psi hydrogen pressure for 2 h. The reaction mixture was filtered over Celite and rinsed with methanol/ethyl acetate. The filtrate was concentrated to give 1.88 g of 3-oxo-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester as a light grey oil which was used without further purification.

Workup

  1. filtrationThe reaction mixture was filtered over Celite
  2. washrinsed with methanol/ethyl acetate
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-cca10e12d43c4bd3a062e188a51df9bf
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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