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

Participants

Reaction Steps

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.

Provenance & Evidence