134623-91-9

Basic information

• Product Name: benzoylecgonine
• Synonyms: benzoylecgonine
• CAS NO: 134623-91-9
• Molecular Weight: 289.331
• Mol File: 134623-91-9.mol

Chemical Properties

• CAS DataBase Reference: benzoylecgonine(CAS DataBase Reference)
• NIST Chemistry Reference: benzoylecgonine(134623-91-9)
• EPA Substance Registry System: benzoylecgonine(134623-91-9)

Safety Data

• Hazardous Substances Data: 134623-91-9(Hazardous Substances Data)

Upstream product

• 47195-07-3 (+)-cocaine 
• 208037-93-8 (S)-dibenzyl 2-(1-benzyl-5-(tert-butoxycarbonyl)pyrrolidin-2-ylidene)succinate 
• 208038-10-2 (1S,2S,3R,5R)-3-Benzoyloxy-2-carbamoyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester 
• 208038-06-6 (1S,2R,6R,8R)-5-Oxa-4,11-diaza-tricyclo[6.2.1.0^2,6]undec-3-ene-3,11-dicarboxylic acid 11-tert-butyl ester 3-ethyl ester 
• 208038-07-7 (1S,2R,6R,8R)-5-Oxa-4,11-diaza-tricyclo[6.2.1.0^2,6]undec-3-ene-3,11-dicarboxylic acid 11-tert-butyl ester 
• 208038-09-9 (1S,2S,3R,5R)-2-Carbamoyl-3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester 
• 208038-11-3 Benzoic acid (1S,2S,3R,5R)-2-carbamoyl-8-aza-bicyclo[3.2.1]oct-3-yl ester 
• 208037-98-3 (1S,5R)-8-Benzyl-2-hydroxy-8-aza-bicyclo[3.2.1]oct-2-ene-3-carboxylic acid methyl ester 
• 208038-08-8 (1S,2R,3R,5R)-2-Cyano-3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester 
• 208038-02-2 (1S,5R)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone 
• 208038-03-3 tert-butyl (1S,5R)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate 
• 208038-01-1 (1S,5R)-8-benzyl-8-azabicyclo[3.2.1]octan-2-one 
• 208038-12-4 Benzoic acid (1S,2S,3R,5R)-2-carbamoyl-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester 

Downstream Products

• 47195-07-3 (+)-cocaine 

Relevant articles and documents

METHODS FOR PRODUCING HYDROXYALKYL TROPANE ESTERS

This invention provides a method for preparing a hydroxyalkyl tropane ester, comprising: (a) contacting a tropane and 1,1'-carbonyldiimidazole to produce an activated tropane ester; (b) contacting the activated tropane ester with an excess of an alkanediol to form a reaction mixture; and (c) maintaining the reaction mixture at a temperature and for a sufficient time for the activated tropane ester to react with the alkanediol to form the corresponding hydroxyalkyl tropane ester. This method may be used to produce hydroxyalkyl derivatives of tropanes such as benzoylecgonine, ecgonine and ecgonidine.

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.