HCID 19738093, compound → HCID 19738102, compound

Participants

Reaction Steps

A mixture of ethyl-3-methyl-8-isopropyl-2-azabicyclo[2.2.2]oct-7-ene-6-carboxylate (21.4 g, 78 mmol), acetic acid (200 mL) and platinum oxide (2.1 g) was placed on a Parr hydrogenator at 44 psi of hydrogen pressure for 41/4 hours. The catalyst was removed by filtration and the solvent was removed in vacuo. The residue was dissolved in water, neutralized with NH4OH to a pH of 10 and the mixture was extracted with CH2Cl2 (3×50 mL). The organic layers were combined, washed with brine and dried over MgSO4. The solvent was removed in vacuo to afford 18.1 g (97%) of ethyl 3-methyl-8-isopropyl-2-azabicyclo-[2.2.2]octane-6-carboxylate. The product was dissolved in ethanol and treated with 6.9N ethanolic HCl to afford 10.2 g of the hydrochloride salt as a white solid, m.p. 157.5°-158.5° C.

Provenance & Evidence