134452-61-2

Upstream product

• 185385-13-1 1-carbomethoxy-5-methoxy-L-proline methyl ester 
• 129397-98-4 (5R)-5-Heptyl-1-methoxycarbonyl-L-proline methyl ester 
• 134353-96-1 (2S,5R)-5-Heptyl-2-hydroxymethyl-1-methoxycarbonylpyrrolidine 
• 147-85-3 L-proline 
• 74761-41-4 (S)-1-(methoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 693-25-4 n-pentylmagnesium bromide 
• 141764-09-2 Benzenesulfonic acid 2-((2S,5R)-1-benzenesulfonyl-5-ethyl-pyrrolidin-2-yl)-ethyl ester 
• 141764-08-1 2-[(2S,5R)-5-Ethyl-1-((R)-1-phenyl-ethyl)-pyrrolidin-2-yl]-ethanol 
• 141764-07-0 [5-Ethyl-1-((S)-1-phenyl-ethyl)-pyrrolidin-2-yl]-acetic acid methyl ester 
• 141764-06-9 (E)-6-Oxo-oct-2-enoic acid methyl ester 
• 762-47-0 7-methyl-6-octen-3-one 
• 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 
• 83541-81-5 (S)-dimethyl pyrrolidine-1,2-dicarboxylate 

Relevant academic research and scientific papers

A novel method for chirospecific synthesis of 2,5-disubstituted pyrrolidines

One-pot ring formation using (R)-1 or (S)-1 as a nucleophile and homochiral glycidyl triflate (R)-2 or (S)-2 as an electrophile provides a pivotal intermediate 4 which can be transformed into a 2,5-disubstituted pyrrolidine with any desired stereochemistr

A new route to trans 2,5-dialkylpyrrolidines

Benzylic amines 8 react with ketoenoates 7 yielding, after reduction of the primary adducts, 2,5-dialkylpyrrolidines 9 (trans isomer predominating). This reaction has been applied to the synthesis of trans 2-heptyl-5-ethylpyrrolidine, a component of the venom of fire ant (Solenopsis punctaticeps).

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).