124016-67-7

Basic information

• Product Name: (±)-Norsedamine
• Synonyms: (±)-Norsedamine
• CAS NO: 124016-67-7
• Molecular Formula: C₁₃H₁₉NO
• Molecular Weight: 205.3
• Mol File: 124016-67-7.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (±)-Norsedamine(CAS DataBase Reference)
• NIST Chemistry Reference: (±)-Norsedamine(124016-67-7)
• EPA Substance Registry System: (±)-Norsedamine(124016-67-7)

Safety Data

• Hazardous Substances Data: 124016-67-7(Hazardous Substances Data)

Upstream product

• 1462-92-6 6-methyl-2,3,4,5-tetrahydro-pyridine 
• 100-52-7 benzaldehyde 
• 4801-58-5 N-hydroxypiperidine 
• 130721-64-1 (Z)-1-phenyl-2-piperidin-2-ylideneethanone 
• 30800-90-9 1-phenyl-2-(piperidin-2-yl)ethan-1-one 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 134040-02-1 (R)-2-((R)-2-Hydroxy-2-phenyl-ethyl)-piperidine-1-carboxylic acid methyl ester 
• 34418-91-2 2,3,4,5-tetrahydropyridine N-oxide 
• 70546-85-9 2-phenyl-3,3a,4,5,6,7-hexahydro-2H-isoxazolo<2,3-a>pyridine 
• 76469-99-3 1-(carbomethoxy)-2-phenacylpiperidine 
• 138371-96-7 tert-butyl 2-(2-oxo-2-phenylethyl)piperidine-1-carboxylate 
• 119910-09-7 N-tert-butoxycarbonyl-2-ethoxypiperidine 
• 85908-96-9 2-oxopiperidine-1-carboxylic acid tert-butyl 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 
• 1415-36-7 (-)-norsedamine 
• 131697-74-0 (2S,3aR)-8-Benzyl-3a-methyl-2-phenyl-hexahydro-isoxazolo[2,3-a]pyridin-8-ium; bromide 
• 127983-46-4 cis-6-methyl-8-phenyl-9-oxa-1-azabicyclo<4.3.0>nonane 
• 497-88-1 sedamine 
• 111528-22-4 (1R,3R)-1-(4-Nitro-phenyl)-3-phenyl-hexahydro-pyrido[1,2-c][1,3]oxazine 
• 127983-45-3 6-(2'-hydroxy-2'-phenylethyl)-2,3,4,5-tetrahydropyridine 

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.

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed amidoalkylation of silylenolethers. Stereocontrolled syntheses of (+/-)-sedamine and (+/-)-norsedamine

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed addition of 1-trimethylsilyloxy-1-phenylethene to N-ethoxycarbonyl- and N-tert-butoxycarbonyl-2-ethoxypiperidines (3a and 3b, respectively) afforded the corresponding ketocarbamates 4a and 4b, in excellent yields. Stereoselective conversion to (±)-norsedamine (7) and (±)-sedamine (8) is described.