138662-60-9

Basic information

• Product Name: 2-Piperidinecarboxylicacid,5-hydroxy-,(2R,5S)-(9CI)
• Synonyms: 2-Piperidinecarboxylicacid,5-hydroxy-,(2R,5S)-(9CI);(2R,5S)-5-Hydroxy-2-piperidinecarboxylic acid;(2R, 5S)-5-Hydroxypiperidine-2-carboxylic acid
• CAS NO: 138662-60-9
• Molecular Formula: C₆H₁₁NO₃
• Molecular Weight: 145.16
• Product Categories: CARBOXYLICACID
• Mol File: 138662-60-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 354.8±42.0 °C(Predicted)
• Appearance: /
• Density: 1.299
• PKA: 2.31±0.40(Predicted)
• CAS DataBase Reference: 2-Piperidinecarboxylicacid,5-hydroxy-,(2R,5S)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Piperidinecarboxylicacid,5-hydroxy-,(2R,5S)-(9CI)(138662-60-9)
• EPA Substance Registry System: 2-Piperidinecarboxylicacid,5-hydroxy-,(2R,5S)-(9CI)(138662-60-9)

Safety Data

• Hazardous Substances Data: 138662-60-9(Hazardous Substances Data)

Usage

Description

2-Piperidinecarboxylic acid, 5-hydroxy, (2R,5S)-(9CI) is a chemical compound with the molecular formula C6H11NO3. It is a derivative of piperidinecarboxylic acid and contains a hydroxy group. 2-Piperidinecarboxylicacid,5-hydroxy-,(2R,5S)-(9CI) has a specific stereochemistry, with a 2R,5S configuration. This chemical is used in the synthesis of pharmaceuticals and organic compounds, and it may have potential applications in medicinal chemistry. Its specific properties and potential uses make it a valuable compound for research and development in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
2-Piperidinecarboxylic acid, 5-hydroxy, (2R,5S)-(9CI) is used as a building block for the synthesis of various pharmaceuticals and organic compounds. Its unique structure and stereochemistry make it a valuable component in the development of new drugs and therapeutic agents.
Used in Medicinal Chemistry Research:
2-Piperidinecarboxylic acid, 5-hydroxy, (2R,5S)-(9CI) is used as a research compound in medicinal chemistry. Its specific properties and potential applications make it a promising candidate for the development of new drugs and therapeutic agents, particularly in the areas of central nervous system disorders, cardiovascular diseases, and other medical conditions.
Used in Chemical Industry:
2-Piperidinecarboxylic acid, 5-hydroxy, (2R,5S)-(9CI) is used as an intermediate in the synthesis of various organic compounds. Its unique structure and stereochemistry make it a valuable component in the development of new chemical products and materials.

Upstream product

• 15069-92-8 5-hydroxypicolinic acid 
• 87179-81-5 (-)-(5S)-5-(tert-butyldimethylsilanyloxy)piperidin-2-one 
• 138565-96-5 methyl (2R,5S)-5-hydroxy-N-methoxycarbonyl-piperidine-2-carboxylate 
• 154049-29-3 methyl (2S,5S)-5-t-butyldimethylsilyloxy-N-methoxycarbonyl-piperidine-2-carboxylate 
• 1429476-44-7 (5S)-dimethyl 5-(tert-butyldimethylsilanyloxy)-5,6-dihydropyridine-1,2(4H)-dicarboxylate 
• 1429476-43-6 (3S)-methyl 6-[(diphenoxyphosphoryl)oxy]-3-(tert-butyldimethylsilanyloxy)-3,4-dihydropyridine-1(2H)-carboxylate 
• 138565-91-0 (5S)-methyl 5-(tert-butyldimethylsilanyloxy)-2-oxopiperidine-1-carboxylate 
• 115514-62-0 dimethyl 5-hydroxy-piperidine-1,2-dicarboxylate 
• 13096-31-6 rac-(2R*,5S*)-5-hydroxypiperidine-2-carboxylic acid 

Downstream Products

• 50439-45-7 (2S,5R)-5-hydroxy-2-piperidinecarboxylic acid 
• 138662-60-9 2R,5S-5-hydroxy-piperidine-2-carboxylic acid 

Relevant articles and documents

Synthesis of unnatural 2R,5S-5-hydroxypipecolic acid via homochiral acyliminium ion-pipecolic acids - Part III

Stereoselective functionalization of S-5-hydroxy-2-piperidone 1 via acyliminium ion was demonstrated to maintain the unnatural enantiomer of trans-5-hydroxypipecolic acid 6.

Complementary and stereodivergent approaches to the synthesis of 5-hydroxy- and 4,5-dihydroxypipecolic acids from enantiopure hydroxylated lactams

We describe two complementary and stereodivergent routes, from commercially available and inexpensive starting materials, for the synthesis of 4,5-dihydroxy- and 5-hydroxypipecolic acids based on the chemistry of lactam-derived enol phosphates. The synthesis of the 4,5-cis-4,5- dihydroxypipecolic acids required the preparation from 2-deoxy-D- and -L-ribose of the enantiopure cis-(4S,5R)- and -(4R,5S)-4,5-dihydroxy-δ-valerolactam, respectively. These new chiral synthons are potentially useful for the synthesis of other natural products. The key step is the Pd-catalyzed methoxycarbonylation reaction of the enol phosphates generated from these lactams. This reaction provided enecarbamate esters that were easily converted by stereoselective reduction to the target compounds. The synthesis of the 4,5-trans-4,5-dihydroxypipecolic acid, as well as of 5-hydroxypipecolic acids, was realized from a known (S)-5-hydroxy-δ-valerolactam derivative and, for the dihydroxylated compound, required a highly stereoselective allylic bromination reaction of the enecarbamate ester obtained by methoxycarbonylation of the enol phosphate. The preparation of the (4R,5S) enantiomer of the cis-4,5-dihydroxy-δ-valerolactam from 2-deoxy-L-ribose, alongside the fact that (R)-5-hydroxy-δ-valerolactam can be prepared from (R)-(-)-γ-hydroxymethyl-γ-butyrolactone, means our approach allows for the synthesis of all stereoisomers of these compounds, which can be employed as conformationally constrained scaffolds in drug discovery. The stereoselective synthesis of 5-hydroxy- and 4,5-dihydroxypipecolic acids was accomplished by sequential Pd-catalysed methoxycarbonylation and stereoselective reduction of enantiopure hydroxylated lactam-derived enol phosphates obtained from both enantiomers of commercially available γ-hydroxymethyl-γ- butyrolactone and 2-deoxyribose. Copyright