497-88-1

Basic information

• Product Name: (αS,2S)-1-Methyl-α-phenyl-2-piperidineethanol
• Synonyms: (-)-Sedamine;(αS,2S)-1-Methyl-α-phenyl-2-piperidineethanol;rac-(R*)-α-[(1-Methylpiperidine-2β*-yl)methyl]benzyl alcohol;rac-1-Methyl-2α*-[(S*)-β-hydroxyphenethyl]piperidine
• CAS NO: 497-88-1
• Molecular Formula: C₁₄H₂₁NO
• Molecular Weight: 219.32264
• Mol File: 497-88-1.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 331.1°C at 760 mmHg
• Flash Point: 147.9°C
• Appearance: /
• Density: 1.024g/cm³
• Vapor Pressure: 6.38E-05mmHg at 25°C
• Refractive Index: 1.535
• CAS DataBase Reference: (αS,2S)-1-Methyl-α-phenyl-2-piperidineethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (αS,2S)-1-Methyl-α-phenyl-2-piperidineethanol(497-88-1)
• EPA Substance Registry System: (αS,2S)-1-Methyl-α-phenyl-2-piperidineethanol(497-88-1)

Safety Data

• Hazardous Substances Data: 497-88-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H21NO/c1-15-10-6-5-9-13(15)11-14(16)12-7-3-2-4-8-12/h2-4,7-8,13-14,16H,5-6,9-11H2,1H3/t13-,14-/m0/s1

Upstream product

• 50-00-0 formaldehyd 
• 1415-36-7 (-)-norsedamine 
• 807373-66-6 (2S)-2-((2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-phenylethyl)-1-methylpiperidine 
• 2508-29-4 5-hydroxypentylamine 
• 221022-83-9 2-(1-methyl-1,2,5,6-tetrahydropyridin-2-yl)-1-phenylethanol 
• 495-47-6 (±)-norsedamine 
• 79-22-1 methyl chloroformate 
• 101113-68-2 (+/-)-sedaminone 
• 138371-97-8 (1SR,2SR) N-tert-butoxycarbonyl-2-(β-hydroxy-β-phenylethyl)piperidine 
• 109-06-8 α-picoline 
• 73853-37-9 1-phenyl-2-(piperidin-2-yl)ethan-1-ol 
• 100-52-7 benzaldehyde 
• 2294-74-8 1-phenyl-2-pyridin-2-yl-ethanol 
• 57147-18-9 1-methyl-2-ethoxy-6-piperidone 

Downstream Products

• 70561-76-1 (±)-allosedamine 
• 67008-23-5 (2R)-2-((2R)-2-hydroxy-2-phenylethyl)-1-methylpiperidine 

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.

Enantioselective Synthesis of (+)-α-Conhydrine and (-)-Sedamine by L-ProlineCatalysed α-Aminooxylation

An efficient organocatalytic approach to the enantioslective synthesis of two important piperidine alkaloids, namely (+)α-conhydrine (98% ee) and (-)-sedamine (95 % ee), by L-pro-line-catalysed α-aminooxylation of aldehydes has been developed. The strategy involves an intramolecular cyclization to construct the piperidine core.

Hydroformylation of homoallylic azides: A rapid approach toward alkaloids

(Chemical Equation Presented) Unprecedented hydroformylation of homoallylic azides combined with useful one-pot operations provides an expeditive access to alkaloids.