217323-82-5

Basic information

• Product Name: (1R,2R,4R)-4-bromo-2-(6-chloropyridin-3-yl)cyclohexanamine
• Synonyms: (1R,2R,4R)-4-bromo-2-(6-chloropyridin-3-yl)cyclohexanamine
• CAS NO: 217323-82-5
• Molecular Weight: 289.603
• Mol File: 217323-82-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (1R,2R,4R)-4-bromo-2-(6-chloropyridin-3-yl)cyclohexanamine(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,4R)-4-bromo-2-(6-chloropyridin-3-yl)cyclohexanamine(217323-82-5)
• EPA Substance Registry System: (1R,2R,4R)-4-bromo-2-(6-chloropyridin-3-yl)cyclohexanamine(217323-82-5)

Safety Data

• Hazardous Substances Data: 217323-82-5(Hazardous Substances Data)

Upstream product

• 1370320-04-9 (+)-tert-butyl N-[(1R,4S)-2-bromo-4-[(tert-butyldimethylsilyl)oxy]cyclohex-2-en-1-yl]carbamate 
• 1370320-03-8 C₁₃H₂₄BrNO₃Si 
• 174817-06-2 cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohex-3-ene 
• 108-86-1 bromobenzene 
• 67451-62-1 cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene 
• 1370320-06-1 (+)-tert-butyl N-[(1R,4S)-2-(6-chloropyridin-3-yl)-4-hydroxycyclohex-2-en-1-yl]carbamate 
• 1370320-05-0 (+)-tert-butyl N-[(1R,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-(6-chloropyridin-3-yl)cyclohex-2-en-1-yl]carbamate 
• 211503-87-6 (1S,4R)-5-(6-Chloro-pyridin-3-yl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester 
• 211503-90-1 (1S,4R,5R)-5-(6-Chloro-pyridin-3-yl)-2-oxa-3-aza-bicyclo[2.2.2]octane-3-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester 
• 211503-85-4 (1S,4R,5R)-5-(6-Chloro-pyridin-3-yl)-2-oxa-3-aza-bicyclo[2.2.2]octane-3-carboxylic acid tert-butyl ester 
• 211503-84-3 2-chloro-5-(1,5-cyclohexadienyl)pyridine 
• 3727-48-8 2-bromocyclohexa-1,3-diene 
• 69045-79-0 2-choro-5-iodopyridine 
• 371247-42-6 (4R)-3-{[(2S,1R,3R,4R)-6-aza-1-(triethylsilyloxy)-3-(6-chloro(3-pyridyl))-5-oxobicyclo[2.2.2]oct-2-yl]carbonyl}-4-benzyl-1,3-oxazolidin-2-one 

Downstream Products

• 140111-52-0 epibatidine 

Relevant articles and documents

Stereoselective Conjugate Addition of the Lithium Anion of N-Allyl Imine to Unsaturated Esters: Application to the Enantiospecific Total Synthesis of (-)-Epibatidine

A regio- and diastereoselective conjugate addition of the lithium anion of N-allyl imine (prepared from allylamine and benzophenone) to α,β-unsaturated esters in good yields is reported. The reaction was general and provided the γ-amino esters resulting from the regioselective C-C bond formation between the α-carbon to the nitrogen in the imine and the β-carbon of the unsaturated ester. Synthetic utility of the formed products was illustrated in the nonracemic total synthesis of the bioactive alkaloid (-)-epibatidine.

Synthesis of (-)-epibatidine

matrix presented The synthesis of (-)-epibatidine has been accomplished utilizing a highly exo-selective asymmetric hetero Diels-Alder reaction. The key steps employed to transform the resulting bicycle into the natural product include a fluoride-promoted fragmentation and a Hofmann rearrangement.

Asymmetric total synthesis of (-)-epibatidine

An enantioselective approach to (-)-epibatidine based on asymmetric hetero Diels-Alder cycloaddition with an N-acylnitroso dienophile bearing 8- (2-naphthyl)menthol as a chiral source, wherein π-π stacking interaction between the naphthyl and nitrosocarbonyl groups may contribute to facial control, is described.