1415-36-7

Basic information

• Product Name: (αS,2S)-α-Phenyl-2-piperidineethanol
• Synonyms: (S)-2-[(2S)-2-Piperidinyl]-1-phenylethanol;(αS,2S)-α-Phenyl-2-piperidineethanol
• CAS NO: 1415-36-7
• Molecular Formula: C₁₃H₁₉NO
• Molecular Weight: 205.3
• Mol File: 1415-36-7.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (αS,2S)-α-Phenyl-2-piperidineethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (αS,2S)-α-Phenyl-2-piperidineethanol(1415-36-7)
• EPA Substance Registry System: (αS,2S)-α-Phenyl-2-piperidineethanol(1415-36-7)

Safety Data

• Hazardous Substances Data: 1415-36-7(Hazardous Substances Data)

Usage

Description

(αS,2S)-α-Phenyl-2-piperidineethanol, commonly known as fentanyl, is a synthetic opioid analgesic with potent narcotic and analgesic properties. It is designed to act on the central nervous system to provide pain relief, sedation, and relaxation. Due to its high potency and effectiveness, fentanyl is a valuable asset in the medical field for managing severe pain. However, it also carries a high risk of abuse, addiction, and overdose, which has led to its classification as a Schedule II controlled substance.

Uses

Used in Pain Management:
(αS,2S)-α-Phenyl-2-piperidineethanol is used as an analgesic agent for the management of severe pain associated with surgery, cancer, or chronic conditions. Its high potency compared to other opioids like morphine makes it a valuable tool in medical settings for patients experiencing intense pain.
Used in Anesthesia:
In the field of anesthesia, (αS,2S)-α-Phenyl-2-piperidineethanol is used as an adjunct to general anesthesia to enhance the effects of sedation and pain relief during surgical procedures.
Used in Palliative Care:
Fentanyl is also utilized in palliative care to alleviate the suffering of patients with terminal illnesses, providing comfort and improving their quality of life.
Used in Drug Delivery Systems:
To address the concerns of abuse and addiction, various drug delivery systems have been developed for (αS,2S)-α-Phenyl-2-piperidineethanol. These systems, such as transdermal patches and lozenges, aim to control the release of the drug and reduce the potential for misuse.

Upstream product

• 495-47-6 (±)-norsedamine 
• 112653-25-5 (1S,4R)-1-<(2S)-2<(2S)-2-Hydroxy-2-phenyl-1-ethyl>-1-piperidylcarbonyl>-4,7,7-trimethyl-2-oxa-bicyclo<2.2.1>heptan-3-on 
• 2294-74-8 (S)-1-phenyl-2-(pyridin-2-yl)ethan-1-ol 
• 934472-40-9 1-phenyl-2-[1-(toluene-4-sulfonyl)-piperidin-2-yl]-ethanol 
• 934472-39-6 [1-(toluene-4-sulfonyl)-piperidin-2-yl]-acetaldehyde 
• 934472-38-5 (S)-N-tosyl-2-piperidinylethanol 
• 934472-44-3 1-phenyl-2-[1-(toluene-4-sulfonyl)-piperidin-2-yl]-ethanol 
• 934472-37-4 2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-(toluene-4-sulfonyl)-piperidine 
• 934472-57-8 4-nitro-benzoic acid 1-phenyl-2-[1-(toluene-4-sulfonyl)-piperidin-2-yl]-ethyl ester 
• 934472-53-4 4-nitro-benzoic acid 1-phenyl-2-[1-(toluene-4-sulfonyl)-piperidin-2-yl]-ethyl ester 
• 1620-53-7 1-phenyl-2-pyridin-2-ylethanone 
• 2294-74-8 1-phenyl-2-pyridin-2-yl-ethanol 
• 250591-25-4 acetic acid 1-phenyl-2-pyridin-2-yl-ethyl ester 
• 250591-26-5 Acetic acid (S)-1-phenyl-2-pyridin-2-yl-ethyl ester 

Downstream Products

• 495-47-6 1-phenyl-2-[(2S)-piperidin-2-yl]-(1R)-ethan-1-ol 
• 112653-26-6 (1S)-1-Phenyl-2<(2R)-2-piperidyl>ethanol 
• 111612-22-7 (1R)-1-Phenyl-2<(2R)-2-piperidyl>ethanol 
• 134040-02-1 (S)-2-((S)-2-Hydroxy-2-phenyl-ethyl)-piperidine-1-carboxylic acid methyl ester 
• 127983-45-3 6-(2'-hydroxy-2'-phenylethyl)-2,3,4,5-tetrahydropyridine 
• 497-88-1 sedamine 
• 111528-22-4 (1R,3R)-1-(4-Nitro-phenyl)-3-phenyl-hexahydro-pyrido[1,2-c][1,3]oxazine 
• 497-88-1 (-)-sedamine 
• 934472-22-7 2-(2-hydroxy-2-phenyl-ethyl)-piperidine-1-carboxylic acid benzyl ester 
• 153401-05-9 (S)-2-((S)-2-Acetoxy-2-phenyl-ethyl)-5-oxo-piperidine-1-carboxylic acid methyl ester 
• 153401-04-8 (2S,5R)-2-((S)-2-Acetoxy-2-phenyl-ethyl)-5-hydroxy-piperidine-1-carboxylic acid methyl ester 
• 165674-73-7 (2S,5S)-5-Hydroxy-2-((S)-2-hydroxy-2-phenyl-ethyl)-piperidine-1-carboxylic acid methyl ester 
• 54784-75-7 6-Episedinone 
• 67010-71-3 (–)-sedinone 

Relevant articles and documents

Decarboxylative Conjunctive Cross-coupling of Vinyl Boronic Esters using Metallaphotoredox Catalysis

The synthesis of complex alkyl boronic esters through conjunctive cross-coupling of vinyl boronic esters with carboxylic acids and aryl iodides is described. The reaction proceeds under mild metallaphotoredox conditions and involves an unprecedented decarboxylative radical addition/cross-coupling cascade of vinyl boronic esters. Excellent functional-group tolerance is displayed, and application of a range of carboxylic acids, including secondary α-amino acids, and aryl iodides provides efficient access to highly functionalized alkyl boronic esters. The decarboxylative conjunctive cross-coupling was also applied to the synthesis of sedum alkaloids.

Studies on the Eschenmoser coupling reaction and insights on its mechanism. Application in the synthesis of Norallosedamine and other alkaloids

The conditions of the Eschenmoser coupling reaction were studied. The formation of the α-thioiminium ion was achieved faster in the presence of an additive (NaI) and dry chloroform as the preferred solvent. The developed conditions were used for the second part of the reaction (the sulfur extrusion itself). The present protocol avoids the formation of byproducts, which were previously described as a major drawback to be overcome. Electrospray ionization tandem mass spectrometry was used to characterize some aspects (intermediates) of the first step of the reaction mechanism. Some reduction conditions were properly tested and the selected conditions were applied to the synthesis of the natural alkaloid Norallosedamine and other derivatives.

Diastereoselective, one-pot synthesis of γ-amino alcohols from ketimines

Deprotonation of ketimines with lithium diisopropyl amide, followed by reaction with aldehydes and subsequent reduction with aluminium hydrides gave γ-amino alcohols with moderate to good syn selectivity. The scope and limitations of this preparative meth