170098-39-2

Usage

Uses

Used in Pharmaceutical Industry:
Methyl (3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinepropanoate is used as a chemical intermediate for the synthesis of various drugs, leveraging its unique structural features to contribute to the development of new medicinal compounds.
Used in Drug Discovery and Development:
Due to its potential biological activities and the importance of its specific stereochemistry, methyl (3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinepropanoate is used as a starting point for research and development in drug discovery. It may lead to the identification of new drug candidates for a range of medical conditions, with further exploration required to understand its full therapeutic potential.

Upstream product

• 149541-62-8 C₁₉H₂₉NO₄ 
• 149541-62-8 cis-(-)-carbonic acid ethyl 1,3-dimethyl-4-[3-(l-methylethoxy)phenyl]-4-piperidinyl ester 
• 145340-44-9 1,3-dimethyl-4-[3-(propan-2-yloxy)phenyl]-4-piperidinol 
• 4629-80-5 1,3-dimethyl-4-piperidinone 
• 131738-73-3 3-(isopropyloxy)phenylbromide 
• 1184775-81-2 C₁₇H₂₇NO*C₂₀H₁₈O₈ 
• 143919-32-8 (R)-1,2,3,4-tetrahydro-1,3-dimethyl-4-<3-(1-methylethoxy)phenyl>pyridine 
• 312329-70-7 4-(3-hydroxyphenyl)-trans-3,4-dimethylpiperidine 
• 292638-85-8 acrylic acid methyl ester 
• 143919-34-0 (3R,5R)-1,3,4-trimethyl-4-<3-(1-methylethoxy)phenyl>piperidine 
• 145678-86-0 (3R,4R)-3,4-dimethyl-4-<3-(1-methylethoxy)phenyl>piperidinecarboxylic acid phenyl ester 
• 119193-19-0 3-[(3R,4R)-3,4-dimethylpiperidin-4-yl]phenol 

Downstream Products

• 808102-09-2 C₁₆H₂₃NO₃ 
• 156130-41-5 ADL 08-0011 
• 145603-86-7 (+)-<<2'(S)-<<4(R)-3-(hydroxyphenyl)-3(R),4-dimethyl-1-piperidinyl>methyl>-1-oxo-3-phenylpropyl>amino>acetic acid 2-methylpropyl ester 
• 156053-89-3 Entereg 
• 156130-44-8 2‐((R)‐2‐benzyl‐3‐((3R,4R)‐4‐(3‐hydroxyphenyl)‐3,4‐dimethylpiperidin‐1‐yl)propanamido)acetic acid 
• 170098-29-0 methyl (αS,3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-α-(phenylmethyl)-1-piperidinepropanoate 

Relevant academic research and scientific papers

Synthesis and characterization of all possible diastereoisomers of alvimopan

Isolation of all possible diastereomers of alvimopan 1 was found to be challenging. In order to perform cut off studies during analytical method development, it was mandatory to synthesize and characterize all the diastereomeric impurities. Here in, our efforts toward the synthesis and isolation of alvimopan (1) diastereomers are discussed.

Compositions containing opioid antagonists

Compositions containing opioid antagonists are disclosed, particularly alvimopan and its active metabolite in solid dosage forms, where the drug is uniformly distributed, achieves the desired bioavailability, and is stable. Methods of preparing and using the compositions containing opioid antagonists are also disclosed. The results are achieved by a combination of processing techniques and component selection.

Compositions containing opioid antagonist

Compositions containing opioid antagonists, particularly alvimopan and its active metabolite, with improved solubility and bioavailability for oral or parenteral administration, injectable dosage formulations, kits, and methods of making and using same are disclosed. In preferred embodiments, invention provides injectable formulations containing opioid antagonists, particularly alvimopan and its active metabolite, having low solubility that may be readily prepared, are stable during storage, and provide maximum levels of opioid antagonists when administered parenterally, particularly via injection. The results are achieved by a combination of processing techniques and component selection.

Synthesis of trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine opioid antagonists: Application of the cis-thermal elimination of carbonates to alkaloid synthesis

Improved syntheses of two trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine opioid antagonists from 1,3-dimethyl-4-piperidinone are described. The 1,3-dimethyl-4-arylpiperidinol 23 was selectively dehydrated in a two step process to the 1,3-dimethyl-4-aryl-1,2,3,6-tetrahydropyridine 26 by the cis-thermal elimination of the corresponding alkyl carbonate derivative at 190°C. In the presence of a basic nitrogen, the success of the elimination was found to be critically dependent upon the nature of the carbonate alkyl group, with Et, i-Bu, and i-Pr being preferred (90% yield). Alkylation of the metalloenamine, formed by deprotonation of 26 with n-BuLi, proceeded regio- and stereospecifically to give the trans-3,4-dimethyl-4-aryl-1,2,3,4-tetrahydropyridine 27, which was converted in three steps to the common intermediate, (3R,4R)-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine. LY255582, a centrally-active opioid antagonist, and LY246736-dihydrate, a peripherally-active opioid antagonist, were prepared from 1,3-dimethyl-4-piperidinone in 11.8% yield (8 steps) and 6.2% yield (12 steps), respectively.

Preparation of 3,4,4-trisubstituted-piperidinyl-N-alkylcarboxylates and intermediates

This invention relates to a process for preparing certain 3,4,4-trisubstituted-piperidinyl-N-alkylcarboxylates, intermediates, and congeners. Finally, the invention provides new 3,4,4-trisubstituted-piperidinyl-N-alkylcarboxylates with formulations and me