1-(1,4-Dioxaspiro[4.5]dec-7ylmethyl)-1,2,3,6-tetrahydro-4-phenylpyridine → 3-[(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)methyl]cyclohexanone

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Reaction Steps

A solution of 1-(1,4-dioxaspiro[4.5]dec-7ylmethyl)-1,2,3,6-tetrahydro-4-phenylpyridine (Step C) (90.4 g) in 500 mL of acetone and 500 mL of 10% aqueous hydrochloric acid solution is refluxed, under nitrogen, for 3 hours. The solvent is evaporated in vacuo and partitioned into ethyl acetate/dilute ammonium hydroxide solution. The organic extract is dried over magnesium sulfate and concentrated, leaving the title compound (68.9 g) as a light pink solid; mp 56°-59° C. Mass spectrum (MS) electron ionization (EI) 269 (m, 41%), 172 (100%).

Provenance & Evidence