182138-13-2

Upstream product

• 501-53-1 benzyl chloroformate 
• 255897-11-1 methyl (1S,4R)-N-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptan-3-one-1-carboxylate 
• 255897-10-0 methyl (1S,3S,4R)-N-(tert-butoxycarbonyl)-3-hydroxy-7-azabicyclo[2.2.1]heptane-1-carboxylate 
• 176965-95-0 (+)-(1'R,2'S,5'R)-8'-phenylmenthyl (1S,5S,8S)-3-methyl-exo-8-iodo-2-oxa-4-azabicyclo<3.3.1>non-3-ene-5-carboxylate 
• 182137-75-3 (1S,4R)-3-Oxo-7-aza-bicyclo[2.2.1]heptane-1,7-dicarboxylic acid 7-benzyl ester 1-tert-butyl ester 
• 255897-08-6 (1'R,2'S,5'R)-8'-phenylmenthyl (1S,3S,4R)-3-acetoxy-7-azabicyclo[2.2.1]heptane-1-carboxylate 

Downstream Products

• 163513-98-2 (-)-(1R,4S)-tert-butyl 2-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate 
• 182138-16-5 (1R,4S)-2-Oxo-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Asymmetric synthesis of conformationally constrained 4-hydroxyprolines and their applications to the formal synthesis of (+)-epibatidine

This report describes the synthesis of enantiomerically pure (1S,3S,4R)- and (1S,3R,4R)-3-hydroxy-7-azabicyclo[2.2.1]heptane-1-carboxylic acids, two new conformationally constrained 4-hydroxyprolines, using a straightforward synthetic route and starting f

Chirospecific synthesis of conformationally constrained 7-azabicycloheptane amino acids by transannular alkylation

A new method is reported for the chirospecific preparation of optically pure 1-carboxy-7-azabicycloheptane amino acids for the generation of peptidomimetics as conformational probes. The method allows for the multigram preparation of these amino acid analogues through use of a thiolactam sulfide contraction and a transannular alkylation sequence as the key C-C bond-forming steps, starting from L-glutamic acid. The route provides access to two common intermediates, 7-(benzyloxycarbonyl)-1-carboxy-7-azabicyclo[2.2.1]-3-heptane and (1S,4R)-7-(benzyloxycarbonyl)-1-carboxy-7-azabicyclo[2.2.1]-3-heptanon e tert-butyl ester, for elaboration to symmetrical and chiral amino acid homologues, respectively. Decarboxylation of the C-1 carboxy unit of the latter intermediate also demonstrated the applicability of the method for a short, chirospecific preparation of a (+)-epibatidine intermediate, (1S,4R)-7-(tert-butyloxycarbonyl)-1-carboxy-7-azabicyclo[2.2.1]3-hepta none.