1283098-14-5

Basic information

• Product Name: (1R,2R,3S,5S)-3-benzoyloxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester
• Synonyms: (1R,2R,3S,5S)-3-benzoyloxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester
• CAS NO: 1283098-14-5
• Molecular Weight: 389.448
• Mol File: 1283098-14-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,2R,3S,5S)-3-benzoyloxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,3S,5S)-3-benzoyloxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester(1283098-14-5)
• EPA Substance Registry System: (1R,2R,3S,5S)-3-benzoyloxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester(1283098-14-5)

Safety Data

• Hazardous Substances Data: 1283098-14-5(Hazardous Substances Data)

Upstream product

• 208037-78-9 (1R,5S)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester 
• 148533-48-6 (1R,2R,3S,5S)-3-hydroxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester 
• 98-88-4 benzoyl chloride 
• 1283098-13-4 (3aS,3bR,5aS,6aS)-3-methoxy-7-azabicyclo[3.2.1]octane[2,3-d]isoxazole-7-carboxylic acid tert-butyl ester 
• 1283098-09-8 (3aS,3bR,5aS,6aS)-3-bromo-7-azabicyclo[3.2.1]octane[2,3-d]isoxazole-7-carboxylic acid tert-butyl ester 
• 1283098-11-2 (7aR,10R,12S)-7a,8,9,10-tetrahydro-10-vinyl-12-phenyl-12H-naphtho[1,2-e]pyrrolo[2,1-b][1,3]oxazine 
• 1283098-16-7 (7aR,10R,12S)-7a,8,9,10-tetrahydro-10-ethynyl-12-phenyl-12H-naphtho[1,2-e]pyrrolo[2,1-b][1,3]oxazine 
• 1042368-71-7 C₂₆H₂₇NO 
• 1042368-49-9 (2S,5R)-2-allyl-5-vinylpyrrolidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 50-36-2 Cocaine 

Relevant articles and documents

Total synthesis of (-)-cocaine and (-)-ferruginine

Total synthesis of tropane alkaloids (-)-cocaine and (-)-ferruginine were accomplished in nine steps each and in 55% and 46% overall yields, respectively, starting from the known Betti base derivative (+)-(7aR,10R,12S)-10-(1H- benzotriazol-1-yl)-7a,8,9,10-tetrahydro-12-phenyl-12H-naphtho[1,2-e]pyrrolo[2, 1-b][1,3]oxazine. In this novel route, RCM reaction and 1,3-dipolar cycloaddition were employed as key steps for the enantioselective construction of tropane skeleton and the regioselective introduction of 3-bromo-2-isoxazoline ring as masked cis-2,3-disubstituents. To obtain the desired precursor (2S,5R)-2-allyl-5-vinylpyrrolidine for RCM reaction, we developed a general and practical method for the preparation of enantiopure cis-2,5-disubstituted pyrrolidines bearing alkene- and/or alkyne-containing substituents. We also offered two highly efficient pathways for the conversion of the 3-bromo-2-isoxazoline ring into the desired cis-2,3-disubstituted groups in (-)-cocaine and (-)-ferruginine.