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Pyrrolidine (also known as tetrahydropyrrole, azolidine, and azacyclopentane) is a five-membered saturated heterocyclic organic compound containing four carbon atoms and one nitrogen atom in the ring. The pyrrolidine ring is present as a core skeleton in some natural amino acids like L-proline and L-hydroxyproline. Pyrrolidines are better nucleophiles than diethylamine, principally because of the less hindered lone pair. The pKa value of pyrrolidine, 11.27 is typical of amine bases. Pyrrolidines are very reactive towards aldehydes and ketones, forming enamines through a nucleophilic addition reaction.
Pyrrolidine is present as a core structure in various drugs, and these drugs have received interest due to their wide range of promising biological activities like antitumor, analgesic, anti-inflammatory, antimicrobial, antioxidant, and antihistaminic activities. The pyrrolidine ring is present in carbepenem antibiotics like meropenem and ertapenem. Chiral pyrrolidines play a significant role both as chiral building blocks for auxiliaries as well as key structures relevant to biologically active substances. The pyrrolidine ring has also been found in many natural alkaloids such as nicotine, cuscohygrine, benzoylecgonine, ecgonidine, ecgonine, dihydrocuscohygrine, and hygrine.