Uses
(5S)-5-Hydroxy-2-piperidinone is used in the enantioselective synthesis of peptides containing cyclopropane pipecolic acid, which can be useful as proline mimetics for probing protein-ligand interactions and generating novel bioactive compounds.
Synthesis
The general procedure for the synthesis of (S)-5-hydroxypiperidin-2-one from the compound (CAS:24211-53-8) was as follows: azide 13 (1.5 g, 10.62 mmol) was dissolved in anhydrous methanol and 20% Pd(OH)2 (0.037 g, 0.53 mmol) was added. The reaction mixture was stirred at 25°C for 24 h under hydrogen (1 atm) atmosphere. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the catalyst was removed by diatomaceous earth filtration and the filtrate was concentrated under reduced pressure to afford the crude product (S)-5-hydroxypiperidin-2-one. The crude product was purified by column chromatography using ethyl acetate and methanol (9:1, v/v) as eluent to finally obtain pure (S)-5-hydroxypiperidin-2-one 14 (1.19 g, 98% yield).
References
[1] Synthetic Communications, 2015, vol. 45, # 13, p. 1559 - 1565
[2] Tetrahedron, 1995, vol. 51, # 21, p. 5935 - 5950
[3] Tetrahedron Letters, 2005, vol. 46, # 8, p. 1247 - 1249
[4] Synthesis, 1986, vol. NO. 3, p. 232 - 233
[5] Journal of Organic Chemistry, 1985, vol. 50, # 6, p. 896 - 899
