213532-95-7

Usage

Uses

Used in Pharmaceutical Synthesis:
(6R)-6-(Hydroxymethyl)-2-piperidinone is utilized as a building block in the synthesis of various pharmaceuticals and organic compounds. Its unique structure allows for the creation of a wide range of derivatives, enhancing the diversity of chemical entities that can be developed for medicinal applications.
Used in Chiral Synthesis:
As a chiral building block, (6R)-6-(Hydroxymethyl)-2-piperidinone is employed in the synthesis of certain drugs, where the specific stereochemistry is crucial for the desired biological activity and therapeutic efficacy.
Used in Chemical Research:
(6R)-6-(Hydroxymethyl)-2-piperidinone has been explored for its potential biological properties, making it a valuable compound in various fields of chemical research. Its exploration contributes to the understanding of structure-activity relationships and the development of new chemical entities with specific biological targets.
Used in Drug Development:
In the field of drug development, (6R)-6-(Hydroxymethyl)-2-piperidinone serves as a key intermediate in the preparation of novel drug candidates. Its unique structural features and chiral nature facilitate the design and synthesis of innovative therapeutic agents with improved pharmacological profiles.

Upstream product

• 183890-34-8 methyl (R)-6-oxopiperidine-2-carboxylate 
• 213532-99-1 (R)-5-Azido-6-(tert-butyl-diphenyl-silanyloxy)-hexanoic acid 4-methoxy-benzyl ester 
• 213532-97-9 (S)-6-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-hexanoic acid 4-methoxy-benzyl ester 
• 213532-96-8 (S)-5,6-Dihydroxy-hexanoic acid 4-methoxy-benzyl ester 
• 187851-95-2 (4-methoxyphenyl)methyl hex-5-enoate 
• 72002-30-3 (R)-6-oxo-piperidine-2-carboxylic acid 
• 7620-28-2 D-2-aminoadipic acid 
• 209257-74-9 (6R)-6-[(tert-butyldiphenylsilyl)oxymethyl]piperidin-2-one 

Relevant academic research and scientific papers

Lactams as prostanoid receptor ligands. Part 4: 2-Piperidones as selective EP4 receptor agonists

2-Piperidones were prepared bearing heptanoic acid or a thioether heptanoic acid at the 1-position as well as appropriately substituted at the 6-position to mimic the structure of prostaglandins. The stereochemical purity at the 6-position was determined to be ≥95% ee for an advanced synthetic intermediate. The 2-piperidones were identified as potent agonists at the EP4 prostanoid receptor. They displayed a high affinity (K i 5-130 nM) at EP4 and subtype selectivity.

EP4 receptor agonist, compositions and methods thereof

This invention relates to potent selective agonists of the EP4 subtype of prostaglandin E2 receptors, their use or a formulation thereof in the treatment of glaucoma and other conditions, which are related to elevated intraocular pressure in the eye of a patient. This invention further relates to the use of the compounds of this invention for mediating the bone modeling and remodeling processes of the osteoblasts and osteoclasts.

EP4 receptor agonist, compositions and methods thereof

This invention relates to potent selective agonists of the EP4 subtype of prostaglandin E2 receptors, their use or a formulation thereof in the treatment of glaucoma and other conditions, which are related to elevated intraocular pressure in the eye of a patient. This invention further relates to the use of the compounds of this invention for mediating the bone modeling and remodeling processes of the osteoblasts and osteoclasts.

Practical asymmetric synthesis of both enantiomers of 6-(hydroxymethyl)piperidin-2-one

A practical asymmetric synthesis of both enantiomers of 6 (hydroxymethyl)piperidin-2-one 1 is described. Asymmetric dihydroxylation (AD) of alkenyl ester 2 using the (DHQ)2AQN ligand provides diol (5S)-3 in ≤95% ee after recrystallisation. This diol can subsequently be transformed into (6R)-1 using a five step reaction sequence. By employing (DHQD)2AQN [1,4-bis(dihydroquininyl)anthraquinone] in the initial AD reaction, (6S)-1 can be prepared in an analogous fashion.