AbstractThe synthesis of the 3‐substitued tetrahydropyrazolopyridin‐4‐ylalkyl iodides7a, 7b, 8aand8bas well as their behavior towards anionic cyclization conditions have been investigated. An (enolendo)‐exo‐tet‐type ring closure only proceeds when a seven‐membered ring is annulated (9b, 10b). Otherwise, treatment of the β‐keto ester7awith NaH results in O‐alkylation to yield the stereoelectronically favored (Z)‐enol ether13a, which can be isomerized to the thermodynamically more stable (E) isomer13b. Various attemps to achieve ring closure of the methyl ketone8afailed; instead, β‐elimination is observed. Annulation of a six‐membered carbocycle is acchieved when the triester17is treated by a Dieckmann condensation to give the