67008-23-5

Basic information

• Product Name: Sedamine
• Synonyms: (1R)-1-Phenyl-2-[(2R)-1-methyl-2-piperidinyl]ethanol;(1R)-1-Phenyl-2-[[(2R)-1-methylhexahydropyridine]-2β-yl]ethanol;(1R)-2-[(2R)-1-Methyl-2-piperidinyl]-1-phenylethanol
• CAS NO: 67008-23-5
• Molecular Formula: C₁₄H₂₁NO
• Molecular Weight: 219.32
• Mol File: 67008-23-5.mol
• Article Data: 26

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Sedamine(CAS DataBase Reference)
• NIST Chemistry Reference: Sedamine(67008-23-5)
• EPA Substance Registry System: Sedamine(67008-23-5)

Safety Data

• Hazardous Substances Data: 67008-23-5(Hazardous Substances Data)

Upstream product

• 497-88-1 sedamine 
• 98712-01-7 (-)-(2R)-N-carbomethoxynorsedaminone 
• 50-00-0 formaldehyd 
• 111612-22-7 (1R)-1-Phenyl-2<(2R)-2-piperidyl>ethanol 
• 311772-70-0 (R)-2-((R)-2-hydroxy-2-phenylethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 639458-46-1 (R)-2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 639458-44-9 (S,S)-2-(2-hydroxy-2-phenyl-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 847833-48-1 (3R,5R)-3-phenylhexahydro-3H-pyrido[1,2-c][1,3]oxazin-1-one 
• 934472-15-8 2-(2-hydroxy-2-phenyl-ethyl)-piperidine-1-carboxylic acid benzyl ester 
• 934472-12-5 [1-(toluene-4-sulfonyl)-piperidin-2-yl]-acetaldehyde 
• 934472-11-4 (R)-N-tosyl-2-piperidinylethanol 
• 934472-14-7 1-phenyl-2-[1-(toluene-4-sulfonyl)-piperidin-2-yl]-ethanol 
• 934472-13-6 1-phenyl-2-[1-(toluene-4-sulfonyl)-piperidin-2-yl]-ethanol 
• 934472-10-3 2-(1-t-butyldimethylsilyloxyethyl)-1-(4-methylphenylsulfonyl)-piperidine 

Downstream Products

• 70561-76-1 (±)-allosedamine 
• 497-88-1 (-)-sedamine 

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.

Stereoselective total synthesis of the piperidine alkaloids, (+)-coniine, (+)-pseudoconhydrine, and (+)-sedamine through a common intermediate

The stereoselective total synthesis of the piperidine alkaloids, (+)-coniine, (+)-pseudoconhydrine and (+)-sedamine has been achieved through a common intermediate generated from butane-1,4-diol. The synthetic sequence involves a Maruoka asymmetric allylation and ring-closing metathesis as the key steps.

A rapid access to (±)-sedamine and some original N -benzyl unsaturated analogues

Reduction of N-alkyl-2-(2-hydroxy-2-phenylethyl)pyridinium salts using excess of sodium triacetoxyborohydride afforded exclusively the corresponding tetrahydropyridine derivative bearing a piperidine ring with a double bond in the 3,4-position. Furthermore, under these conditions, syn-1,3-amino alcohols were obtained in good yield and diastereoselectivity. Georg Thieme Verlag Stuttgart · New York.