132697-07-5

Upstream product

• 149710-65-6 1,4,5,6-Tetrahydro-4-(3-methoxyphenyl)-N,N,1,4-tetramethyl-3-pyridinemethanamine 
• 132621-45-5 4-(3-Methoxy-phenyl)-1,4,5-trimethyl-1,2,3,4-tetrahydro-pyridine 
• 149710-64-5 1,2,3,4-Tetrahydro-4-(3-methoxyphenyl)-1,4-dimethylpyridine 
• 73224-22-3 1-methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine 
• 10365-98-7 3-methoxyphenylboronic acid 
• 951240-62-3 C₉H₁₄NO₃SBr 
• 951240-61-2 C₉H₁₅NO₃S 
• 220503-22-0 C₁₄H₁₉ON 
• 951240-71-4 C₁₃H₁₇ON 
• 951240-66-7 C₁₇H₂₅O₃SN 
• 951240-65-6 C₁₀H₁₈NO₂SBr 
• 951240-64-5 C₁₃H₂₅NO₆SBrP 
• 951240-63-4 C₉H₁₆NO₃SBr 

Downstream Products

• 149655-33-4 (3R,4R)-4-(3-methoxyphenyl)-3,4-dimethylpiperidine 

Relevant academic research and scientific papers

First asymmetrie synthesis of frans-3,4-dimethyl-4-arylpiperidines

The first asymmetric synthesis of the trans-3,4-dimethyl-4-arylpiperidine opioid antagonist scaffold is reported. C-3 stereochemistry was established via CBS reduction and stereoselective anti-SN2′ cuprate displacement of the derived allylic phosphonate. The resultant vinyl bromide was then elaborated to the target compound by Suzuki coupling and frans-selective 4-methylation. Extension of this methodology should allow general enantioselective access to highly substituted piperidine ring systems.

Structure-activity relationships of trans-3,4-dimethyl-4-(3- hydroxyphenyl)piperidine antagonists for μ- and κ-opioid receptors

A series of racemic N-substituted trans-3,4-dimethyl-4-(3- hydroxyphenyl)piperidines were evaluated for opioid agonist and antagonist activity at μ and κ receptors. Several highly potent μ and κ antagonists were discovered; however, no compounds with high selectivity for either the μ or κ receptor were identified. Importantly, no derivative was found to have significant opioid agonist activity. Two derivatives were resolved, and the activities of the enantiomers were investigated. Only a limited stereochemical effect on opioid receptor selectivities was observed. The structure-activity relationships described establish the existence of an important lipophilic binding site distal to the nitrogen for both μ and κ receptors and confirm the pure opioid antagonist pharmacophore nature of the trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine structure.