1428766-60-2

Upstream product

• 18303-04-3 N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide 
• 1428766-59-9 2-bromomethyl-1-tosylaziridine-2-carboxaldehyde 
• 100-46-9 benzylamine 
• 1092540-27-6 ethyl 2-(bromomethyl)-1-tosylaziridine-2-carboxylate 
• 1092540-15-2 ethyl 2,3-dibromo-2-[(tosylamino)methyl]propanoate 
• 1092540-02-7 ethyl 2-{[(4-methylbenzene)sulfonamido]methyl}acrylate 
• 1428766-57-7 ethyl 2-({(N-tert-butoxycarbonyl)[N-toluene-4-sulfonyl]amino}methyl)prop-2-enoate 

Downstream Products

• 1428766-64-6 N-[1-benzyl-2-(bromomethyl)aziridin-2-ylmethyl]-4-methylbenzenesulfonamide 
• 1428766-68-0 1-benzyl-5-(toluene-4-sulfonyl)-1,5-diazaspiro[2.3]hexane 
• 1428766-72-6 1-benzyl-1,5-diazaspiro[2.3]hexane 

Relevant academic research and scientific papers

Synthesis of 1,5-diazaspiro[2.3]hexanes, a novel diazaspirocyclic system

The convenient synthesis of 1,5-diazaspiro[2.3]hexanes, as new structurally challenging strained diazaspirocyclic compounds, was developed starting from easily accessible ethyl 2-(bromomethyl)-1-tosylaziridine-2-carboxylate. The key transformations in the developed four-step sequence involved a chemoselective reduction of the functionalized ethyl 1-tosylaziridine-2-carboxylate to the corresponding β-bromo aldehyde and an aza-Payne-type rearrangement of intermediate N-tosyl 2-(aminomethyl)aziridines into N-alkyl 2-(aminomethyl) aziridines. A final base-mediated cyclization of the formed bromo amines gave efficient access to the new diazaspirocyclic system.