208037-77-8

Basic information

• Product Name: (1R,5S)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone
• Synonyms: (1R,5S)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone
• CAS NO: 208037-77-8
• Molecular Weight: 225.288
• Mol File: 208037-77-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,5S)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,5S)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone(208037-77-8)
• EPA Substance Registry System: (1R,5S)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone(208037-77-8)

Safety Data

• Hazardous Substances Data: 208037-77-8(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 208037-76-7 (1R,5S)-8-benzyl-8-azabicyclo[3.2.1]octan-2-one 
• 208037-90-5 (1R,5S)-2-Hydroxy-8-aza-bicyclo[3.2.1]oct-2-ene-3,8-dicarboxylic acid 8-tert-butyl ester 3-methyl ester 
• 208037-73-4 (2R,5S)-5-[1'-(2'-methoxycarbonyl)ethyl]proline methyl ester 
• 208037-72-3 (2R,5S)-5-(2-Carboxy-ethyl)-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 208037-71-2 2-[(R)-1-Benzyl-5-tert-butoxycarbonyl-pyrrolidin-(2Z)-ylidene]-succinic acid dibenzyl ester 
• 208037-89-2 (2R,5S)-N-(tert-butyloxycarbonyl)-5-[1'-(2'-methoxycarbonyl)ethyl]proline methyl ester 
• 208037-74-5 (2R,5S)-N-benzyl-5-[1'-(2'-methoxycarbonyl)ethyl]proline methyl ester 
• 208037-75-6 methyl 8-benzyl-2-hydroxy-8-azabicyclo[3.2.1]oct-2-ene-3-carboxylate 

Downstream Products

• 155748-84-8 RTI-128 
• 208037-88-1 Benzoic acid (1R,2R,3S,5S)-2-carbamoyl-8-aza-bicyclo[3.2.1]oct-3-yl ester 
• 208037-87-0 (1R,2R,3S,5S)-3-Benzoyloxy-2-carbamoyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester 
• 519-09-5 benzylecgonine 
• 50-36-2 Cocaine 

Relevant articles and documents

Enantiospecific Synthesis of Natural (-)-Cocaine and Unnatural (+)-Cocaine from D- And L-Glutamic Acid

Natural (-)-cocaine and unnatural (+)-cocaine have been synthesized enantiospecifically from D-and L-glutamic acid, respectively. The axial-equatorial substitutents were introduced by a stereo-and regiospecific dipolar cycloaddition to the corresponding (1R,5S)- and (1S,5R)-N-BOC-nortropenes with (ethoxycarbonyl)formonitrile N-oxide. A sequence of subsequent stereochemically controlled transformations converted the fused isoxazoline to the requisite β-hydroxy ester. Synthesis of the key intermediate N-BOC-nortropenes involved construction of the 8-azabicyclo[3.2.1]octane framework by Dieckmann condensation of cis-5-substituted D- and L-proline esters. For comparison, (1R,5S)-N-BOC-nortropene also was derived by degradation from natural cocaine. The cis-5-substituted D- and L-proline esters were obtained by sulfide contraction and subsequent catalytic hydrogenation to induce stereospecifically the C-5 stereochemistry from D- and L-thiopyroglutamate, which in turn were prepared from D- and L-glutamic acids, respectively.