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The condensation of arylacetonitriles with cyclic ketones using aqueous NaOH or KOH under phase transfer catalysis gives almost quantitative yields of cycloalkanols. This protocol is utilized for a practical synthesis of the antidepression drug, venlafaxine 1.
The first condensations of N-methoxycarboxamides (component A) with aliphatic acetals (component B) are described. Depending upon the conditions, the hemiaminal type products (AB) can usually be isolated. Conducting the condensations with 2equiv of acetal affords β-(N-methoxy)amido aldehydes (type ABB products). A condensation using anisole (component C) afforded a product of type ABC.
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