Potassium Carbonate → 2-Methyl-1-azabicyclo(2.2.2)octan-3-one

Participants

Reaction Steps

A mixture of 10.1 g (58.4 mmol) of 2-methylene-1-azabicyclo[2.2.2]octan-3-one hydrochloride hydrate, 8.1 g of K2CO3 and 100 mg of PtO2 in 100 mL of MeOH was hydrogenated at 10–15 psi H2 for about 1 hr. The solution was filtered through dicalite and the solvent was evaporated in vacuo. The residue was dissolved in CHCl3 and again filtered through dicalite. The filtrate was evaporated in vacuo to give 4.7 g (58% yield) of 2-methyl-1-azabicyclo[2.2.2]octan-3-one Compound 8A as a yellow oil. 1H NMR (CDCl3) 1.3 (d, 3H), 2.0 (m, 4H), 2.4 (t, 1H), 2.9 (m, 1H), 3.05 (, 1H), 3.2 (m, 3H). This material was used without further purification in the next step.

Provenance & Evidence