182138-16-5

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
(1R,4S)-2-Oxo-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid benzyl ester is used as a building block in pharmaceutical research and drug development due to the presence of the azetidin-2-one moiety, which is a common structural feature in many bioactive compounds.
Used in Organic Synthesis:
(1R,4S)-2-Oxo-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid benzyl ester is used as a versatile building block in organic synthesis, as the benzyl ester group can be selectively cleaved to reveal the carboxylic acid functionality, allowing for further chemical reactions and modifications.

Upstream product

• 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 
• 182138-13-2 (1S,4R)-N-(benzyloxycarbonyl)-7-azabicyclo[2.2.1]heptan-3-one-1-carboxylic acid 

Downstream Products

• 163513-98-2 (-)-(1R,4S)-tert-butyl 2-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate 

Relevant academic research and scientific papers

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.