title: Lithium tetramethylpiperidide
text: # Lithium tetramethylpiperidide
  
  Lithium tetramethylpiperidide (often abbreviated LiTMP or LTMP) is a chemical compound with the molecular formula $LiC_9H_{18}N.$ It is used as a non-nucleophilic base, being comparable to LiHMDS in terms of steric hindrance.
  
  ## Synthesis
  
  It is synthesised by the deprotonation of 2,2,6,6-tetramethylpiperidine with n-butyllithium at −78 °C. Recent reports show that this reaction can also be performed 0 °C. The compound is stable in a THF/ethylbenzene solvent mixture and is commercially available as such.
  
  ## Structure
  
  Like many lithium reagents it has a tendency to aggregate, forming a tetramer in the solid state.
  
  