1032237-00-5

Basic information

• Product Name: (2S,4R)-4-hydroxypiperidine-2-carboxylic acid hydrochloride
• Synonyms: (2S,4R)-4-hydroxypiperidine-2-carboxylic acid hydrochloride
• CAS NO: 1032237-00-5
• Molecular Formula: C₆H₁₁NO₃*ClH
• Molecular Weight: 181.61738
• Mol File: 1032237-00-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 202-204 °C (decomp)
• Appearance: /
• CAS DataBase Reference: (2S,4R)-4-hydroxypiperidine-2-carboxylic acid hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4R)-4-hydroxypiperidine-2-carboxylic acid hydrochloride(1032237-00-5)
• EPA Substance Registry System: (2S,4R)-4-hydroxypiperidine-2-carboxylic acid hydrochloride(1032237-00-5)

Safety Data

• Hazardous Substances Data: 1032237-00-5(Hazardous Substances Data)

Usage

General Description

(2S,4R)-4-hydroxypiperidine-2-carboxylic acid hydrochloride is a chemical compound that consists of a piperidine ring with a hydroxyl group and a carboxylic acid functional group. It is a stereochemically defined form of the compound and has a hydrochloride salt form. (2S,4R)-4-hydroxypiperidine-2-carboxylic acid hydrochloride may have potential pharmaceutical applications due to the presence of the piperidine ring, which is a common structural motif in many biologically active compounds. The hydrochloride salt form is often used for solubility and stability purposes, making it suitable for use in pharmaceutical formulations. The compound can be used as an intermediate in the synthesis of various pharmaceuticals and may also have potential therapeutic properties.

Upstream product

• 1031883-65-4 dimethyl (2S,4R)-4-hydroxypiperidine-1,2-dicarboxylate 
• 1031883-70-1 dimethyl (2S,4R)-4-(tert-butyldimethylsilyloxy)piperidine-1,2-dicarboxylate 
• 1204587-88-1 dimethyl (2S,4R)-4-tert-butoxypiperidine-1,2-dicarboxylate 
• 1204587-85-8 dimethyl (R)-4-tert-butoxy-5,6-dihydropyridine-1,2(4H)-dicarboxylate 

Downstream Products

• 1212688-40-8 (2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxypiperidine-2-carboxylic acid 

Relevant articles and documents

Enantioselective Synthesis of cis and trans 4-Aminopipecolic Acids as γ-Amino Acids for the Construction of Cyclic RGD-Containing Peptidomimetics Antagonists of αVβ3 Integrin

A stereodivergent strategy to obtain enantiopure cis and trans 4-aminopipecolic acids (4-APAs) in a suitably protected form for peptide synthesis has been devised starting from a common, known precursor in turn easily prepared from commercial (R)-4-cyano-3-hydroxybutyric acid ethyl ester. The two isomers were efficiently obtained in 40 percent and 23 percent overall yields, respectively, in seven and ten steps. To demonstrate their usefulness in peptidomimetic synthesis, both 4-APA isomers were incorporated as γ-amino acids in a cyclic RGD-containing sequence, although for the trans 4-APA isomer a further amino acid in the sequence (L-Phe) was needed to allow ring closure. The two cyclopeptides were tested as αVβ3 integrin antagonists in comparison with cilengitide.

Stereoselective synthesis of (2S,4R)-4-hydroxypipecolic acid

A new synthetic route to enantiopure (2S,4R)-4-hydroxypipecolic acid from commercial ethyl (3S)-4-chloro-3-hydroxybutanoate is reported. The synthesis is based on the Pd-catalyzed methoxycarbonylation of a 4-alkoxy-substituted δ-valerolactam-derived vinyl triflate followed by the stereocontrolled hydrogenation of the enamine double bond. The final product was obtained after exhaustive hydrolysis in 20 % yield over 10 steps. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.