114676-96-9

Upstream product

• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 

Downstream Products

• 113451-59-5 (1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester 
• 5260-20-8 (1S,4S)-2,5-Diazabicyclo<2.2.1>heptane dihydrochloride 
• 1429199-67-6 (7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]-2-{[4-(trifluoromethyl)-phenyl]sulfonyl}hexahydropyrrolo[1,2-a]pyrazin-4(1H)-one 
• 1429199-66-5 (7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]-2-{[3-(trifluoromethyl)phenyl]-sulfonyl}hexahydropyrrolo[1,2-a]pyrazin-4(1H)-one 
• 1429200-36-1 tert-butyl (2S,4R)-4-[(5-cyclopropylpyrazin-2-yl)oxy]-2-{[(2-methoxy-2-oxoethyl){[3-(trifluoromethyl)phenyl]sulfonyl}amino]methyl}pyrrolidine-1-carboxylate 
• 1429296-66-1 (7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]-2-[3-(trifluoromethyl)benzyl]hexahydropyrrolo[1,2-a]pyrazin-3(4H)-one 
• 1429296-34-3 (7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]-2-[4-(trifluoromethyl)benzoyl]hexahydropyrrolo[1,2-a]pyrazin-4(1H)-one 
• 211298-50-9 (2S,4R)-2-Azidomethyl-4-(biphenyl-2-ylmethoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

A practical synthesis of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane

The rigid piperazine homologue 2,5-diazabicyclo[2.2.1]heptane (DBH) finds extensive application in medicinal chemistry and pharmaceutical research, but access to this scaffold is non-trivial. This letter details a concise synthetic sequence that gives ready access to DBH on gram scale. The route features a Staudinger reduction of an azide to facilitate a transannular cyclisation.