HCID 10221000, compound → 8-(1,1-Dimethylethyl) 2-methyl 8-azabicyclo[3.2.1]octane-2,8-dicarboxylate

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Reaction Steps

8-Azabicyclo[3.2.1]oct-2-ene-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester from Step 4 (5.9 g, 22 mmol) was dissolved in ethanol (100 mL), to which palladium (10% on charcoal, 0.59 g) was added. The resulting mixture was shaken under an atmosphere of hydrogen (50 psi) for 2 hours at room temperature, and was then filtered through a bed of Celite, which was washed with ethyl acetate. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by flash chromatography (silica gel, ethyl acetate/hexane) to provide 8-azabicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester as a mixture of endo and exo isomers as a colorless oil (5.8 g, 97% yield).

Provenance & Evidence