223424-24-6

Basic information

• Product Name: (3S,4S)-4-(3-Isopropoxy-phenyl)-1,3,4-trimethyl-piperidine
• CAS NO: 223424-24-6
• Molecular Weight: 261.407
• Mol File: 223424-24-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (3S,4S)-4-(3-Isopropoxy-phenyl)-1,3,4-trimethyl-piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-4-(3-Isopropoxy-phenyl)-1,3,4-trimethyl-piperidine(223424-24-6)
• EPA Substance Registry System: (3S,4S)-4-(3-Isopropoxy-phenyl)-1,3,4-trimethyl-piperidine(223424-24-6)

Safety Data

• Hazardous Substances Data: 223424-24-6(Hazardous Substances Data)

Usage

Description

(3S,4S)-4-(3-Isopropoxy-phenyl)-1,3,4-trimethyl-piperidine is a chiral piperidine derivative with a molecular formula of C17H29NO. It features a piperidine ring with three methyl substituents and an isopropoxy-phenyl group attached to the fourth position. (3S,4S)-4-(3-Isopropoxy-phenyl)-1,3,4-trimethyl-piperidine is known for its potential pharmacological properties, which may include psychoactive or medicinal applications due to its structural similarity to other piperidine derivatives used in antipsychotics, analgesics, and local anesthetics.

Uses

Used in Pharmaceutical Industry:
(3S,4S)-4-(3-Isopropoxy-phenyl)-1,3,4-trimethyl-piperidine is used as a potential active pharmaceutical ingredient for the development of various medications. Its structure suggests that it may have psychoactive properties or other pharmacological activities, making it a candidate for further research and development in the creation of new drugs.
Used in Research and Development:
In the field of medicinal chemistry, (3S,4S)-4-(3-Isopropoxy-phenyl)-1,3,4-trimethyl-piperidine is used as a compound of interest for exploring its potential biological activities and interactions with various biological targets. This can lead to the discovery of new therapeutic applications and the advancement of pharmaceutical science.

Upstream product

• 77-78-1 dimethyl sulfate 
• 444904-02-3 (S)-1,2,3,6-tetrahydro-1,3-dimethyl-4-[3-(1-methylethoxy)phenyl]pyridine 
• 149541-62-8 cis-(-)-carbonic acid ethyl 1,3-dimethyl-4-[3-(l-methylethoxy)phenyl]-4-piperidinyl ester 
• 131738-73-3 3-(isopropyloxy)phenylbromide 
• 149541-62-8 C₁₉H₂₉NO₄ 
• 145340-44-9 1,3-dimethyl-4-[3-(propan-2-yloxy)phenyl]-4-piperidinol 
• 149541-62-8 Carbonic acid ethyl ester (3R,4S)-4-(3-isopropoxy-phenyl)-1,3-dimethyl-piperidin-4-yl ester 
• 4629-80-5 1,3-dimethyl-4-piperidinone 

Downstream Products

• 145678-87-1 (-)-3(S),4(S)-dimethyl-4-(3-hydroxyphenyl)piperidine 
• 441003-83-4 3-[1-(2S-amino-3-methylbutyl)-3S,4S-dimethyl-4-piperidinyl]phenol 
• 361444-66-8 (3R)-7-hydroxy-N-((1S)-1-{[(3S,4S)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide 
• 441003-84-5 (R)-7-Hydroxy-3-{(S)-1-[(3S,4S)-4-(3-hydroxy-phenyl)-3,4-dimethyl-piperidin-1-ylmethyl]-2-methyl-propylcarbamoyl}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 156130-44-8 2‐((S)‐2‐benzyl‐3‐((3S,4S)‐4‐(3‐hydroxyphenyl)‐3,4‐dimethylpiperidin‐1‐yl)propanamido)acetic acid 
• 156130-44-8 2‐((R)‐2‐benzyl‐3‐((3S,4S)‐4‐(3‐hydroxyphenyl)‐3,4‐dimethylpiperidin‐1‐yl)propanamido)acetic acid 

Relevant articles and documents

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.

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.