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
• Article Data: 18

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 
• 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 
• 3105-95-1 pipecolinic acid 
• 121895-18-9 (S)-2-amino-6-hydroxyhexanoic acid methyl ester hydrochloride 

Downstream Products

• 917507-80-3 (2S,5S)-N-[(benzyloxy)carbonyl]-5-hydroxy-2-piperidinecarboxylic acid 
• 1523606-41-8 (1R,4R)-2-oxa-5-azabicyclo[2.2.2]octane oxalate 
• 1523606-41-8 (1S,4S)-2-oxa-5-azabicyclo[2.2.2]octane oxalate 

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.

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.

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.