50439-45-7

Basic information

• Product Name: (2S,5R)-trans-5-Hydroxypiperidine-2-carboxylic acid
• Synonyms: (2S,5R)-trans-5-Hydroxypiperidine-2-carboxylic acid;(2S,5R)-5-Hydroxypipecolic acid;(2S,5R)-5-hydroxypiperidine-2-carboxylic acid
• CAS NO: 50439-45-7
• Molecular Formula: C₆H₁₁NO₃
• Molecular Weight: 145.16
• Mol File: 50439-45-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 354.8±42.0 °C(Predicted)
• Appearance: /
• Density: 1.299
• PKA: 2.31±0.40(Predicted)
• CAS DataBase Reference: (2S,5R)-trans-5-Hydroxypiperidine-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5R)-trans-5-Hydroxypiperidine-2-carboxylic acid(50439-45-7)
• EPA Substance Registry System: (2S,5R)-trans-5-Hydroxypiperidine-2-carboxylic acid(50439-45-7)

Safety Data

• Hazardous Substances Data: 50439-45-7(Hazardous Substances Data)

Usage

General Description

(2S,5R)-trans-5-Hydroxypiperidine-2-carboxylic acid, also known as (S, R)-trans-5-hydroxy-L-pipecolic acid, is a chemical compound with the molecular formula C6H11NO3. It is a naturally occurring amino acid derivative that is found in certain plant tissues and is a structural component of certain antibiotics and antifungal agents. (2S,5R)-trans-5-Hydroxypiperidine-2-carboxylic acid has potential applications in the pharmaceutical industry for the development of new drugs, particularly for the treatment of neurodegenerative diseases. Its specific biological and pharmacological properties are of interest for further study and potential therapeutic use.

Upstream product

• 13096-31-6 rac-(2R*,5S*)-5-hydroxypiperidine-2-carboxylic acid 
• 84409-89-2 (2S,5R)-N-[(benzyloxy)carbonyl]-5-hydroxy-2-piperidinecarboxylic acid 
• 3105-95-1 pipecolinic acid 
• 2219-28-5 δ-hydroxylysine hydrochloride 
• 15069-92-8 5-hydroxypicolinic acid 
• 504-91-6 2,6-diamino-5-hydroxy-hexanoic acid 
• 59182-85-3 benzyloxycarbonyl-L-baikiain 

Downstream Products

• 84409-89-2 (2S,5R)-N-[(benzyloxy)carbonyl]-5-hydroxy-2-piperidinecarboxylic acid 
• 50439-45-7 (2S,5R)-5-hydroxy-2-piperidinecarboxylic acid 
• 138662-60-9 2R,5S-5-hydroxy-piperidine-2-carboxylic acid 
• 1487347-86-3 (2S,5R)-1-(tert-butoxycarbonyl)-5-hydroxypiperidine-2-carboxylic acid 
• 189952-46-3 (2S,5R)-methyl 5-hydroxypiperidine-2-carboxylate 

Relevant articles and documents

Development of a Stereoselective Synthesis of (1 R,4 R)- and (1 S,4 S)-2-Oxa-5-azabicyclo[2.2.2]octane

Despite the prevalence of morpholine derivatives and bridged heterocycles in medicinally relevant compounds, bridged bicyclic morpholines remain scarce because of the challenges associated with their synthesis. MRK A, an IDH1mut inhibitor for the treatment of glioma, derives its potency in part from substitution of a zigzag 2,5-bicyclic morpholine, 2-oxa-5-azabicyclo[2.2.2]octane, at C8. While existing entries suffered from low yields and lack of stereochemical control, we developed concise stereospecific routes toward both enantiomers of the zigzag morpholine antipode. The key common intermediate in the two routes was a chiral bicyclic lactone, which was readily synthesized following our previous synthesis of relebactam from optically pure (2S,5S)-5-hydroxypiperidine-2-carboxylic acid (HPA). The desired (R,R) enantiomer for incorporation into MRK A required inversion of both stereocenters of the bicyclic lactone intermediate, which was accomplished by epimerization via a crystallization-induced diastereomer transformation process followed by a key Ti(OiPr)4-mediated intramolecular SN2 ring closure. By this method, the (R,R)-zigzag morpholine was synthesized in six steps from HPA in 25% overall yield.

METHOD FOR PRODUCING cis-5-HYDROXY-2-PIPERIDINECARBOXYLIC ACID DERIVATIVE, AND METHOD FOR PURIFYING cis-5-HYDROXY-2-PIPERIDINECARBOXYLIC ACID

The present invention aims to provide a method for purifying cis-5-hydroxy-2-piperidinecarboxylic acid with high purity, and a method for producing its derivative. The present invention provides a method for producing a cis-5-hydroxy-2-piperidinecarboxylic acid derivative, which method comprises a step of converting cis-5-hydroxy-2-piperidinecarboxylic acid into a compound(s) of Formula (1) and/or Formula (2) (wherein R1 represents a protective group for an amino group, and R2 represents a C1-C6 alkyl group), and a method for purifying cis-5-hydroxy-2-piperidinecarboxylic acid.

Stereoselective preparation of cyclic l-amino acids

The invention concerns a method for producing a cyclic L-amino acid of formula (I), characterised in that it consists in reacting a L-diamino acid of formula (II) or an enantiomeric mixture comprising such a L-diamino acid and a corresponding D-diamino acid in variable proportions, in the presence of an ornithine cyclodeaminase or a polypeptide homologous to the ornithine cyclodeaminase. 1