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36323

Sigma-Aldrich

(S)-6-Oxo-2-piperidinecarboxylic acid

≥95.0% (HPLC)

Synonym(s):

6-Oxo-L-pipecolic acid, (S)-2-Piperidone-6-carboxylic acid, L-Pyrohomoglutamic acid

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About This Item

Empirical Formula (Hill Notation):
C6H9NO3
CAS Number:
34622-39-4
Molecular Weight:
143.14
MDL number:
MFCD03839863
UNSPSC Code:
12352005
PubChem Substance ID:
329755004
NACRES:
NA.22

Quality Level

100

Assay

≥95.0% (HPLC)

impurities

≤5.0% water

SMILES string

OC(=O)[C@@H]1CCCC(=O)N1

InChI

1S/C6H9NO3/c8-5-3-1-2-4(7-5)6(9)10/h4H,1-3H2,(H,7,8)(H,9,10)/t4-/m0/s1

InChI key

FZXCPFJMYOQZCA-BYPYZUCNSA-N

Application

(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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH0619
BCCJ2892
BCCF8066
BCBX5125
BCBS7325V

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Preparation of optically pure ω-hydroxymethyl lactams
Huang S-B, et al.
Synthetic Communications, 19(20), 3485-3496 (1989)
Rational Design and Asymmetric Synthesis of Potent and Neurotrophic Ligands for FK506-Binding Proteins (FKBPs)
Pomplun S, et al.
Angewandte Chemie (International ed. in English), 54(1), 345-348 (2015)
Carboxymethylproline synthase catalysed syntheses of functionalised N-heterocycles
Hamed RB, et al.
Chemical Communications (Cambridge, England), 46(9), 1413-1415 (2010)

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