129446-23-7

Basic information

• Product Name: (2R,5R)-5-Butyl-2-heptylpyrrolidine
• CAS NO: 129446-23-7
• Molecular Weight: 225.418
• Mol File: 129446-23-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (2R,5R)-5-Butyl-2-heptylpyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5R)-5-Butyl-2-heptylpyrrolidine(129446-23-7)
• EPA Substance Registry System: (2R,5R)-5-Butyl-2-heptylpyrrolidine(129446-23-7)

Safety Data

• Hazardous Substances Data: 129446-23-7(Hazardous Substances Data)

Upstream product

• 129446-22-6 (2R,5R)-5-Butyl-2-heptyl-1-methoxycarbonylpyrrolidine 
• 109-72-8 n-butyllithium 
• 1315127-16-2 (-)-1,1-dimethylethyl (2R,5R)-2-butyl-5-heptylpyrrolidine-1-carboxylate 
• 1315127-14-0 (-)-1,1-dimethylethyl (2S,5R)-2-[(2Z)-but-2-en-1-yl]-5-heptylpyrrolidine-1-carboxylate 
• 1315127-12-8 (-)-1,1-dimethylethyl (2R,5S)-2-heptyl-5-(2-oxoethyl)pyrrolidine-1-carboxylate 
• 1234693-36-7 (-)-1,1-dimethylethyl (2R,5S)-2-heptyl-5-[2-(methyloxy)-2-oxoethyl]pyrrolidine-1-carboxylate 
• 74761-41-4 (S)-1-(methoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 147-85-3 L-proline 
• 134353-98-3 (2R,5S)-2-Heptyl-5-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid methyl ester 
• 134354-04-4 (2S,5R)-5-Heptyl-pyrrolidine-1,2-dicarboxylic acid 1-methyl ester 
• 134353-96-1 (2S,5R)-5-Heptyl-2-hydroxymethyl-1-methoxycarbonylpyrrolidine 
• 83541-81-5 (S)-dimethyl pyrrolidine-1,2-dicarboxylate 
• 129397-98-4 (5R)-5-Heptyl-1-methoxycarbonyl-L-proline methyl ester 
• 185385-13-1 1-carbomethoxy-5-methoxy-L-proline methyl ester 

Downstream Products

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

Relevant articles and documents

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).

(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.