478409-64-2

Basic information

• Product Name: 2-Piperidinecarboxylic acid, 5-hydroxy-, (2S)- (9CI)
• Synonyms: 2-Piperidinecarboxylic acid, 5-hydroxy-, (2S)- (9CI)
• CAS NO: 478409-64-2
• Molecular Formula: C6H11NO3
• Molecular Weight: 145.15644
• Product Categories: ALCOHOL;CARBOXYLICACID
• Mol File: 478409-64-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Piperidinecarboxylic acid, 5-hydroxy-, (2S)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Piperidinecarboxylic acid, 5-hydroxy-, (2S)- (9CI)(478409-64-2)
• EPA Substance Registry System: 2-Piperidinecarboxylic acid, 5-hydroxy-, (2S)- (9CI)(478409-64-2)

Safety Data

• Hazardous Substances Data: 478409-64-2(Hazardous Substances Data)

Upstream product

• 15069-92-8 5-hydroxypicolinic acid 
• 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 
• 59182-85-3 benzyloxycarbonyl-L-baikiain 
• 504-91-6 2,6-diamino-5-hydroxy-hexanoic acid 
• 2219-28-5 δ-hydroxylysine hydrochloride 
• 917507-80-3 (2S,5S)-N-[(benzyloxy)carbonyl]-5-hydroxy-2-piperidinecarboxylic acid 
• 15366-19-5 methyl (S)-2-benzyloxycarbonylamino-6-diazo-5-oxohexanoate 
• 117836-15-4 (S)-2-Benzyloxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid methyl ester 
• 117836-26-7 cis-5(S)-hydroxy-2(S)-N₁-benzyloxycarbonylpipecolic acid methyl ester 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 
• 23632-67-9 (S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid 
• 117836-18-7 (S)-2-Benzyloxycarbonylamino-6-chloro-5-trimethylsilanyloxy-hexanoic acid methyl ester 

Downstream Products

• 189952-46-3 (2S,5S)-methyl 5''-hydroxypiperidine-2-carboxylate 
• 1487347-86-3 1-tert-butoxycarbonyl-5-hydroxypiperidine-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 
• 1510832-15-1 (1S,4S)-5-((2-nitrophenyl)sulfonyl)-2-oxa-5-azabicyclo[2.2.2]octan-3-one 
• 1510832-19-5 4-((2S,5R)-((benzyloxy)amino)piperidine-2-carboxamido)piperidine-1-carboxylic acid tert-butyl ester 
• 1510831-80-7 C₃₁H₄₂N₄O₈S₂ 
• 1510832-11-7 C₃₅H₄₂N₆O₁₂S₂ 
• 1174020-63-3 tert-butyl 4-((1R,2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamido)piperidine-1-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.

Studies on the selectivity of proline hydroxylases reveal new substrates including bicycles

Studies on the substrate selectivity of recombinant ferrous-iron- and 2-oxoglutarate-dependent proline hydroxylases (PHs) reveal that they can catalyse the production of dihydroxylated 5-, 6-, and 7-membered ring products, and can accept bicyclic substrates. Ring-substituted substrate analogues (such hydroxylated and fluorinated prolines) are accepted in some cases. The results highlight the considerable, as yet largely untapped, potential for amino acid hydroxylases and other 2OG oxygenases in biocatalysis.

METHODS OF USING RAD51 INHIBITORS FOR TREATMENT OF PANCREATIC CANCER

This application is directed to inhibitors of RAD51 represented by the following structural formula, and methods for their use, such as to treat pancreatic cancer.

RAD51 Inhibitors

This application is directed to inhibitors of RAD51 represented by the following structural formula, and methods for their use, such as to treat cancer, autoimmune diseases, immune deficiencies, or neurodegenerative diseases.

METHOD FOR PRODUCING 5-HYDROXYPIPERIDINE-2-CARBOXYLIC ACID

A method for producing (2S,5S)/(2R,5R)-5-hydroxypiperidine-2-carboxylic acid represented by formula (10) below: the method including removing the protecting group from the hydroxyl group in a compound represented by formula (7) below: (wherein P represents a protecting group, R3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms) to synthesize a compound represented by formula (8) below: (wherein R3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms).

Synthetic methods for (1S,4S)-2,5-diazabicyclo[2.2.2] octane and derivatives thereof

The invention discloses synthetic methods for (1S,4S)-2,5-diazabicyclo[2.2.2] octane and derivatives thereof, and belongs to the field of organic chemical synthesis. According to the method, 5-hydroxypyrazine-2-formate as a compound II is taken as a raw material, and high selectivity of a reaction is guaranteed through selective protection of hydroxyl and amino groups. A product obtained with the method has high yield, the by-product content is low, and the method is applicable to industrial production.

MANUFACTURING METHOD OF (2S,5S)-5-HYDROXY-2-PIPERIDINECARBOXYLIC ACID AS WELL AS MANUFACTURING INTERMEDIATE OF THE SAME AND METHOD FOR MANUFACTURING THE SAME

PROBLEM TO BE SOLVED: To provide synthesis methods of 5-hydroxy-6-methoxypiperidine-2-carboxylic acid derivatives and 5-oxopiperidine-2-carboxylic acid derivatives more safely than ever by using inexpensive raw ingredients. SOLUTION: In the provided method, a compound expressed by the following formula [X] is manufactured from a compound expressed by the following formula [I] through steps (1) through (9) [either steps (4) and (5) or steps (6) and (7) in the case of steps (4) through (7)]. COPYRIGHT: (C)2015,JPOandINPIT

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.

Regio- and stereoselective oxygenation of proline derivatives by using microbial 2-oxoglutarate-dependent dioxygenases

We evaluated the substrate specificities of four proline cis-selective hydroxylases toward the efficient synthesis of proline derivatives. In an initial evaluation, 15 proline-related compounds were investigated as substrates. In addition to L-proline and L-pipecolinic acid, we found that 3,4-dehydro-L-proline, L-azetidine-2-carboxylic acid, cis-3-hydroxy-L-proline, and L-thioproline were also oxygenated. Subsequently, the product structures were determined, revealing cis-3,4-epoxy-L-proline, cis-3-hydroxy-L-azetidine-2-carboxylic acid, and 2,3-cis-3,4-cis-3,4-dihydroxy-L-proline.

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