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2-(2-Hydroxyethyl)pyridine is a metabolite of the anti-vertigo drug Betahistine. It acts as a reagent for protection of the 5'-phosphate of nucleotides as 2-pyridylethyl (Pet) esters. It is used for carboxyl protection of amino acids. It is also used to cleave such groups as Boc and Fmoc, and also to hydrogenolysis. It was used to prepare mononuclear nickel(II) acetate.
Miha Trdin; Valter Bergant; Ivan Leban; Nina Lah. Two concomitant polymorphs of monomeric nickel acetate with 2-pyridineethanol. Acta Chimica Slovenica. 2012, 59, (3), 478-483.
Takashi Niwa; Hideki Yorimitsu; Koichiro Oshima. Palladium-Catalyzed 2-Pyridylmethyl Transfer from 2-(2-Pyridyl)ethanol Derivatives to Organic Halides by Chelation-Assisted Cleavage of Unstrained Cmath image[BOND]Cmath image Bonds. Angewandte Chemie (International Edition). 2007, 46, (15), 2643-2645.
Reagent for protection of the 5'-phosphate of nucleotides as 2-pyridylethyl (Pet) esters. The group can be introduced by DCC-coupling, is stable to mild base, but can be cleaved by methoxide in pyridine-methanol: Chem. Ber., 103, 1032 (1970).
Has also been used for carboxyl protection of amino acids. Pet esters are stable to both mildly acidic and basic conditions used to cleave such groups as Boc and Fmoc, and also to hydrogenolysis. Cleavage is by quaternization with methyl iodide in the presence of mild base: Tetrahedron Lett., 25, 3971 (1984); Angew. Chem. Int. Ed., 23, 716 (1984). See Appendix 6.
Hazard Statements: H227-H315-H319-H335
Combustible liquid. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P210u-P261-P280a-P305+P351+P338-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.