129446-23-7

Upstream product

• 129446-22-6 (2R,5R)-5-Butyl-2-heptyl-1-methoxycarbonylpyrrolidine 
• 109-72-8 n-butyllithium 
• 129446-24-8 (2R-trans)-2-butyl-5-heptyl-1-phenylsulfonylpyrrolidine 
• 3637-16-9 5-oxododecanoic acid 
• 6093-96-5 methyl 5-oxo-dodecanoate 
• 77569-84-7 1-hydroxy-dodecan-5-one 
• 83541-81-5 (S)-dimethyl pyrrolidine-1,2-dicarboxylate 
• 134353-96-1 (2S,5R)-5-Heptyl-2-hydroxymethyl-1-methoxycarbonylpyrrolidine 
• 134353-98-3 (2R,5S)-2-Heptyl-5-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid methyl ester 
• 74761-41-4 (S)-1-(methoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 1234693-36-7 (-)-1,1-dimethylethyl (2R,5S)-2-heptyl-5-[2-(methyloxy)-2-oxoethyl]pyrrolidine-1-carboxylate 
• 1315127-12-8 (-)-1,1-dimethylethyl (2R,5S)-2-heptyl-5-(2-oxoethyl)pyrrolidine-1-carboxylate 
• 1315127-14-0 (-)-1,1-dimethylethyl (2S,5R)-2-[(2Z)-but-2-en-1-yl]-5-heptylpyrrolidine-1-carboxylate 
• 1315127-16-2 (-)-1,1-dimethylethyl (2R,5R)-2-butyl-5-heptylpyrrolidine-1-carboxylate 

Downstream Products

• 129446-24-8 (2R-trans)-2-butyl-5-heptyl-1-phenylsulfonylpyrrolidine 

Relevant academic research and scientific papers

Chirospecific synthesis of trans-2,5-disubstituted pyrrolidines via stereoselective addition of organocopper reagents to N-acyliminium ions

Reaction of the N-acyliminium ion precursor 1a (derived from S-proline via anodic methoxylation) with RCu in the presence of BF3·Et2O gives preferentially the trans adducts 2 (trans:cis ≥96:4). Using such a procedure, a general synthetic route to (2R, 5R)-trans-2,5-dialkylpyrrolidines has been developed, as exemplified by the chirospecific syntheses of the ant feromones trans 5-butyl-2-heptylpyrrolidine (10a), trans-5-ethyl-2-heptylpyrrolidine (10b) and trans-5-heptyl-2-(5-hexenyl)pyrrolidine (10c).

Enantioselective syntheses of 2,5-disubstituted pyrrolidines based on iridium-catalyzed allylic aminations-total syntheses of alkaloids from amphibian skins

A broadly applicable route to trans-2,5-disubstituted pyrrolidines has been developed. Key steps are an asymmetric iridium-catalyzed allylic amination, a Suzuki-Miyaura coupling, and an intramolecular aza-Michael addition. Enantiomeric excesses in the range of 93-99 % ee have been achieved. Total syntheses of the alkaloids (-)-225 C, (+)- and (-)-223 H (xenovenine), (+)-223 AB, (+)-195 B, and (+)-223 R have been carried out as applications. Copyright

(2R-trans)-2-Butyl-5-heptylpyrrolidine as a potent sigma receptor ligand produced by Streptomyces longispororuber

A potent sigma (σ) receptor ligand was isolated from the culture broth of Streptomyces longispororuber 525. The active compound was identified to be (2R-trans)-2-butyl-5-heptylpyrrolidine by spectroscopic and chemical studies. The compound exhibited high affinity and selectivity for σ receptors. The IC50 values toward σ1, σ2 and dopamine D2 receptors were 2.0, 22.7 and more than 40,000 nM, respectively. Its (2S-trans)- and (±)-cis-isomers, both synthesized, were also found to be high affinity σ ligands.

Diastereo- and enantioselective syntheses of (-)-coniine, (-)-solenopsin A, (-)-solenopsis fugax venom and (-)-xenovenine via deoxygenative decarboxylation of 2-carbonylsultam-substituted N-hydroxy-piperidines and -pyrrolidines

Heating cyclic 2-carbonylsultam-substituted N-hydroxylamines 4 with NaH yields sultam auxiliary 8 and imines 10, which are trapped in situ either by i-Bu2AlH or organocerium reagents to give enantiomerically pure 2-mono- or trans-2,6(2,5)-disubstituted piperidines (pyrrolidines) 11 or 12.