66393-06-4

Upstream product

• 69610-41-9 Boc-L-Pro-H 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 141119-75-7 ((1S,7aR)-5-Oxo-hexahydro-pyrrolizin-1-yl)-carbamic acid tert-butyl ester 
• 877309-50-7 methyl 5-oxo-hexahydro-1H-pyrrolizine-1-carboxylate 
• 933759-72-9 5-Oxo-hexahydro-pyrrolizine-1-carboxylic acid 
• 272438-74-1 1-(tert-butoxycarbonyl)-2-[3-(methoxymethylamino)-propionyl]-pyrrolidine 
• 150435-66-8 2-acryloyl-1-(tert-butoxycarbonyl)-pyrrolidine 
• 220329-69-1 1-(tert-butoxycarbonyl)-2-(1-hydroxy-1-allyl)-pyrrolidine 
• 115186-37-3 tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 15912-22-8 (+/-)-1-hydroxyiminopyrrolizidine 
• 141119-75-7 ((1R,7aR)-5-Oxo-hexahydro-pyrrolizin-1-yl)-carbamic acid tert-butyl ester 

Downstream Products

• 141119-68-8 4-Amino-5-chloro-2-ethoxy-N-(1S,7aS)-hexahydro-pyrrolizin-1-yl-benzamide 
• 141119-68-8 4-Amino-5-chloro-2-ethoxy-N-(1S,7aR)-hexahydro-pyrrolizin-1-yl-benzamide 
• 112513-33-4 (1R,8S)-(+)-absouline 
• 112513-33-4 (1S,8R)-(+)-absouline 
• 134202-57-6 4-Amino-5-chloro-N-(1S,7aR)-hexahydro-pyrrolizin-1-yl-2-methoxy-benzamide 
• 134202-57-6 4-Amino-5-chloro-N-(1S,7aS)-hexahydro-pyrrolizin-1-yl-2-methoxy-benzamide 

Relevant academic research and scientific papers

Synthesis of substituted pyrrolidines and piperidines from endocyclic enamine derivatives. Synthesis of (±)-laburnamine

Functionalization of the α- and β-positions of readily available endocyclic enamine derivatives provides a convenient method for the formation of substituted pyrrolidines and piperidines. α-Alkoxy-β- iodopyrrolidines are formed by the electrophilic addition of iodine to the endocyclic enamine double bond of an N-substituted 2-pyrroline, and nucleophillic attack by an alcohol on the intermediate iodonium ion. The resultant α-alkoxy-β-iodopyrrolidines can be used in radical cyclization reactions to give bicyclic hemiaminal compounds, which can be further elaborated using N-acyliminium chemistry to form α,β-cis- dialkylsubstituted pyrrolidines. A strategy for the incorporation of amino functionality at the β-position was also established by using iodoamination of the enamine double bond, followed by migration of the amine functionality through an aziridination/methanolysis protocol. An alternative method uses an azidomethoxylation protocol using ceric ammonium nitrate (CAN) in the presence of NaN3 and methanol. Formation and trapping of the N-acyliminium ions derived from these substrates, afforded the 3-carbamate and 3-azido-2-substituted products with good diastereoselectivity, with the preferential formation of the trans and cis stereoisomers, respectively. Using the sequential iodoamination, aziridination in methanol and N-acyliminium transformation, trans-3-NHCO2Me-2-allyl-pyrrolidine was prepared, which was used as the key precursor in a synthesis of the natural 1-amidopyrrolizidine alkaloid, (±)-laburnamine.

Synthesis of natural 1-amidopyrrolizidines, absouline and laburnamine, derivatives and aminopyrrolidinoimidazole analogues

Natural 1-amidopyrrolizidines, absouline and laburnamine, were synthesized via stable pyrrolizidin-1-one hydrobromide. Amides, ester derivatives and aminopyrrolidinoimidazole analogues were also prepared and their biological activities tested. (C) 2000 Elsevier Science Ltd.