Acetic Acid → HCID 86605393, compound

Participants

Reaction Steps

To avoid catalytic poisoning during the hydrogenation, the quaternary pyridinium salt was first washed to remove free iodide. 3-{4-[(R)-{[(1S)-1-(methoxycarbonyl)-3-methylbutyl]oxy}(phenyl)methyl]phenyl}-1-methylpyridinium iodide from step 3 in example 36 (3.58 g, 6.6 mmol) was dissolved in dichloromethane (100 mL) and shaken with 5% sodium metabisulfite (30 mL) until the heavy red color dissipated. The organic layer was separated, dried (Na2SO4), filtered and concentrated to recover 3.2 g. of starting material. A mixture of the quaternary salt (3.2 g, 6.0 mmol), methanol (150 mL), acetic acid (800 mg, 12 mmol) and platinum oxide (hydrated) 79-84% (250 mg) was hydrogenated at 60 psi for 48 hours. The mixture was filtered, concentrated and then concentrated 2 times with n-heptane. The residue was chromatographed on silica gel using 5% methanol in dichloromethane to obtain the title compound as a foam.

Provenance & Evidence