95587-13-6

Upstream product

• 95587-14-7 (+)-(S)-trans-2-heptyl-5-butylpyrrolidine 
• 98-09-9 benzenesulfonyl chloride 
• 131403-21-9 (2S,5R)-1-benzyloxycarbony-2-butyl-5-(hydroxymethyl)pyrrolidine 
• 131403-23-1 (2S,5R)-1-benzyloxycarbonyl-2-butyl-5-(1-heptenyl)pyrrolidine 
• 131403-22-0 (2S,5R)-2-Butyl-5-formyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 4762-26-9 hexyltriphenylphosphonium bromide 
• 95513-54-5 1-((2R,5S)-1-Benzyl-5-heptyl-pyrrolidin-2-yl)-butan-1-one 
• 95513-44-3 (2R)-trans-1-benzyl-5-heptylproline 
• 95513-25-0 (2R)-trans-1-benzyl-2-(1-hydroxybutyl)-5-heptylpyrrolidine 
• 95513-33-0 (5S)-1-benzyl-2-cyano-5-heptylpyrrolidine 
• 95513-26-1 (2R)-trans-2-(1-hydroxybutyl)-5-heptylpyrrolidine 
• 95513-28-3 (2R)-trans-1-(phenylsulfonyl)-2-(1-<(phenylsulfonyl)oxy>butyl)-5-heptylpyrrolidine 
• 116558-84-0 (+/-)-trans-2-butyl-5-heptylpyrrolidine 

Downstream Products

• 95587-14-7 (+)-(S)-trans-2-heptyl-5-butylpyrrolidine 

Relevant academic research and scientific papers

(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.

An Efficient Route to Chiral trans-2,5-Dialkylpyrrolidines via Stereoselective Intramolecular Amidomercuration

An intramolecular amidomercuration of α-butylated 4-pentenylcarbamate 5 predominantly provided trans-2,5-disubstituted pyrrolidine 6, which was elaborated to chiral trans-5-butyl-2-alkylpyrrolidines 10 and 13, constituents of ant venoms.

α-Amino Acids as Chiral Educts for Asymmetric Products. Chirospecific Syntheses of the 5-Butyl-2-heptylpyrrolidines from Glutamic Acid

Both enantiomers of trans-5-butyl-2-heptylpyrrolidine, an active and major component in the repellent venom of the ant Solenopsis fugax, have been synthesized with very high diastereomeric and optical purity from glutamic acid.Both enantiomers of the cis isomer also have been synthesized in an extension of our methodology to encompass the preparation of both cis and trans, optically pure, 2,5-disubstituted pyrrolidines and because of their potential entomological interest.Initially, a sulfide contraction process efficiently introduces the first side chain onto a pyroglutamate intermediate.Various strategies to elaborate the second side chain have been developed along with methods to control and establish the relative steroechemistry at C-2 and C-5 of the pyrrolidine ring with high selectivity. 2,5-Dialkyl-1-pyrrolidines, which also have been identified in the ant venom, can be prepared by these processes as well with specific absolute stereochemistry.