269717-63-7

Upstream product

• 74-89-5 methylamine 
• 960599-34-2 dimethyl (+)-(R)-2-[N-benzyl-N-(2-chloroacetyl)amino]pentanedioate 
• 269717-62-6 dimethyl (-)-(S)-2-[N-benzyl-N-(2-chloroacetyl)amino]pentanedioate 
• 56-86-0 L-glutamic acid 
• 23150-65-4 L-glutamic dimethyl ester hydrochloride 
• 100-52-7 benzaldehyde 
• 192655-69-9 dimethyl (S)-2-(benzylamino)pentanedioate 

Downstream Products

• 269717-65-9 (1S,2R,5S)-6-benzyl-2-methoxy-8-methyl-2-(trimethylsiloxy)-6,8-diazabicyclo[3.2.2]nonane-7,9-dione 
• 467229-81-8 [(1S,2R,5S)-(6-benzyl-8-methyl-7,9-dioxo-6,8-diazabicyclo[3.2.2]nonan-2-yl)]methanesulphonate 
• 467229-84-1 (1S,2S,5S)-6-benzyl-2-(dimethylamino)-8-methyl-6,8-diazabicyclo[3.2.2]nonane-7,9-dione 
• 467229-82-9 (1S,2S,5S)-2-azido-6-benzyl-8-methyl-6,8-diazabicyclo[3.2.2]nonane-7,9-dione 
• 467229-83-0 (1S,2S,5S)-2-amino-6-benzyl-8-methyl-6,8-diazabicyclo[3.2.2]nonane-7,9-dione 
• 467229-80-7 (1S,2R,5S)-6-benzyl-2-hydroxy-8-methyl-6,8-diazabicyclo[3.2.2]nonane-7,9-dione 

Relevant academic research and scientific papers

Synthesis of chiral non-racemic 3-(dioxopiperazin-2-yl)propionic acid derivatives

Starting with the proteinogenic amino acid (S)-glutamate (3) a facile, high yielding synthesis of the chiral non-racemic 3-(dioxopiperazin-2-yl)propionates 6, 11, and 14 is presented. Key intermediates in the synthesis of N1-benzyl substituted (dioxopiperazin-2yl)propionates 11 and 14 are the N-monobenzylglutamate 8 and the chloroacetamide 12, which allow introduction of various substituents in position 4 of the piperazine ting. In receptor binding studies with radioligands the 3-(piperazin-2-yl)propanol 15 was found to have promising affinity for σ1-receptors (Ki=66.1 nM).

Synthesis of 6,8-diazabicyclo[3.2.2]nonanes: Conformationally restricted piperazine derivatives

(equation presented) Starting with the proteinogenic amino acid (S)-glutamate, a general method for the synthesis of 3-(piperazin-2-yl)propionic acid esters 7 with various substituents at N-4 of the piperazine ring system is presented. An intramolecular ester condensation of 7 is the key step in the formation of the 6,8-diazabicyclo[3.2.2]nonane derivatives 8-10, which are of interest as conformationally restricted piperazines.