(S)-5-HYDROXY-PIPERIDIN-2-ONE Chemical Properties

Melting point:

123-124℃ (methanol ethyl ether )

Boiling point:

352.3±35.0 °C(Predicted)

Density 

1.199±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

14.21±0.20(Predicted)

Appearance

Off-white to light brown Solid

InChI

InChI=1S/C5H9NO2/c7-4-1-2-5(8)6-3-4/h4,7H,1-3H2,(H,6,8)/t4-/m0/s1

InChIKey

GPRZVNYVEZZOKH-BYPYZUCNSA-N

SMILES

N1C[C@@H](O)CCC1=O

Safety Information

Hazard Codes 

Xi

Risk Statements 

41

Safety Statements 

26-39

(S)-5-HYDROXY-PIPERIDIN-2-ONE Usage And Synthesis

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

(S)-5-HYDROXY-PIPERIDIN-2-ONE(24211-54-9)Related Product Information

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