886449-70-3

Upstream product

• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 850426-34-5 1-tert-butyl 2-methyl 2-(2-oxoethyl)pyrrolidine-1,2-dicarboxylate 
• 147-85-3 L-proline 
• 112348-45-5 1-tert-butyl 2-methyl 2-(prop-2-en-1-yl)pyrrolidine-1,2-dicarboxylate 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 

Relevant academic research and scientific papers

Spirobicyclic diamines. Part 3: Synthesis and metal complexation of proline-derived [4.4]-spirodiamines

The syntheses of racemic and homochiral [4.4]-spirolactams, starting from l-proline, in good yields are described. Reduction of the lactam carbonyl group of spirolactams, containing chiral substituents on the lactam nitrogen, with lithium aluminium hydride, gives?a series of homochiral [4.4]-spirodiamines. The crystal structure of one of these spirodiamines on complexation with zinc chloride was obtained. Interestingly it showed a hydrogen-bonded dimeric structure, where the monomers are diastereoisomeric diamines.

Spirobicyclic diamines 1: synthesis of proline-derived spirolactams via thermal intramolecular ester aminolysis

Proline-derived [4.4]-spirolactams have been synthesised in good yields by a reductive-amination reaction followed by thermal cyclisation of the resulting amine onto the proline ester group in refluxing toluene. The synthesis of the corresponding [4.5]-spirolactams by the same method gave much reduced yields.