138662-60-9

Usage

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

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

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.

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.

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

Synthesis of functionalized 3-hydroxypiperidines

The synthetic versatility of three chemoenzymatically prepared hydroxypiperidine building blocks has been explored, resulting in a library of enantiopure functionalized piperidines. Key steps involved N-acyliminium ion-mediated CC-bond formation and cross-metathesis reactions, after which full deprotection led to the set of free 3-hydroxypiperidines.