Acetic Acid → (+)(4aR,6R,8aS)-1,2,3,4,4a,5,6,7,8,8a-Decahydro-6-((4-methoxyphenyl)methyl)quinoline

Participants

Reaction Steps

(-)-(1'S,4aS,6R,8aS)-1,2,3,4,4a,5,6,7,8,8a-Decahydro-6-((4-methoxyphenyl)methyl-1-(1'-phenylethyl)quinoline (1.32 g, prepared according to Example 14) in n-hexane:MeOH (1:1, 80 ml) with 10% Pd/C (0.2 g) and glacial acetic acid (5 ml) was hydrogenated at 50 psi for 15 hours. The solution was filtered, evaporated under reduced pressure and the residue treated with sodium carbonate solution to give a product which was extracted into ethyl acetate. The ethyl acetate extract was dried (MgSO4) and evaporated to give a gum. This was dissolved in diethyl ether and treated with ethereal HCl. The resulting precipitate was collected by filtration and dried giving the title compound as the hydrochloride salt (0.7 g), mp 226°-8° C. [α]26D =+38° (1% in MeOH).

Provenance & Evidence