208038-05-5

Basic information

• Product Name: C₁₄H₁₉NOSe
• Synonyms: C₁₄H₁₉NOSe
• CAS NO: 208038-05-5
• Molecular Weight: 296.271
• Mol File: 208038-05-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₁₄H₁₉NOSe(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₄H₁₉NOSe(208038-05-5)
• EPA Substance Registry System: C₁₄H₁₉NOSe(208038-05-5)

Safety Data

• Hazardous Substances Data: 208038-05-5(Hazardous Substances Data)

Upstream product

• 74242-55-0 anhydroecgonine hydrochloride 
• 53-21-4 (-)-cocaine hydrochloride 

Downstream Products

• 50-36-2 Cocaine 
• 519-09-5 benzylecgonine 
• 208037-87-0 (1R,2R,3S,5S)-3-Benzoyloxy-2-carbamoyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester 
• 208037-88-1 Benzoic acid (1R,2R,3S,5S)-2-carbamoyl-8-aza-bicyclo[3.2.1]oct-3-yl ester 
• 155748-84-8 RTI-128 
• 208037-81-4 tropidine 

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.