848094-35-9

Upstream product

• 18039-42-4 5-Phenyl-1H-tetrazole 
• 868-72-4 dimethyl (2R,5S)-2,5-dibromohexanedioate 
• 124-04-9 Adipic acid 
• 100-47-0 benzonitrile 
• 111-50-2 Adipic acid dichloride 

Downstream Products

• 1286256-32-3 2-amino-5-(5-phenyl-2H-tetrazol-2-yl)hexanedioic acid hydrochloride 
• 1286256-27-6 dimethyl 2-(1,3-dioxoisoindolin-2-yl)-5-(5-phenyl-2H-tetrazol-2-yl)hexanedioate 

Relevant academic research and scientific papers

Synthesis of new tetrazole-substituted pyroaminoadipic and pipecolic acid derivatives

Racemic 5-aryl- and 5-(arylmethyl)tetrazolyl-substituted pyroaminoadipic and pipecolic acid derivatives were diastereoselectively synthesized from dimethyl meso-2,5-dibromoadipate (1) in good yields under mild reaction conditions. The key step of this reaction sequence is the selective N2-alkylation of 5-substituted tetrazoles with 1. The reactive 2-bromo-5-tetrazolyladipate derivatives 2a-g were generated and treated with sodium azide, followed by Pd/C-catalyzed hydrogenation, to provide lactams 4a-g. The chemoselective reduction of the amide carbonyl group of 4a-g with BH 3, followed by acid hydrolysis, provided 5-tetrazolylpipecolic acids in racemic form. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.