(S)-2-Piperidinone-6-carboxylic acid

Uses

6-Oxo-L-pipecolic Acid is an intermediate in the synthesis of metabolites of lysine developed during aging and in diabetic patients.

Uses

(S)-6-Oxo-2-piperidinecarboxylic acid can be used as a reactant to synthesize:

• Functionalized β-lactam N-heterocycles via carboxymethylproline synthase catalyzed cyclization reactions. Pro-(S)-C⁵ branched [4.3.1] aza-amide bicycles as potential inhibitors for FK506-binding proteins.
• Ethyl (S)-2-(6-oxopiperidin-2-yl)acetate, which is reduced using LiBH₄ to produce optically pure hydroxymethyl lactams.

Synthesis

General procedure for the synthesis of (S)-2-piperidone-6-carboxylic acid from L-2-aminoadipic acid: (a) Mix (S)-2-aminoadipic acid (50 g, 310.25 mmol), acetic acid (100 mL) and water (400 mL) and reflux for 3 hours. The unreacted starting amino acid (24 g) was filtered, the filtrate was evaporated, and the residue was dissolved in hot water (50 mL) and precipitated as crystals after cooling. The crystals were collected by filtration to afford the title intermediate (S)-6-oxopiperidine-2-carboxylic acid (20 g, 45% yield).

References

[1] Chemical and Pharmaceutical Bulletin, 1999, vol. 47, # 11, p. 1525 - 1531
[2] Journal of the American Chemical Society, 1982, vol. 104, # 16, p. 4446 - 4450
[3] Journal of Medicinal Chemistry, 1986, vol. 29, # 9, p. 1654 - 1658
[4] Chemical Communications, 2010, vol. 46, # 9, p. 1413 - 1415
[5] Patent: US2013/287731, 2013, A1. Location in patent: Paragraph 0295; 0296