95587-14-7

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 629-04-9 1-Bromoheptane 
• 195299-15-1 2-cyano-5-oxazolopyrrolidine 
• 108198-76-1 undeca-4,5-dien-1-ol 
• 95513-54-5 1-((2R,5S)-1-Benzyl-5-heptyl-pyrrolidin-2-yl)-butan-1-one 
• 95513-28-3 (2R)-trans-1-(phenylsulfonyl)-2-(1-<(phenylsulfonyl)oxy>butyl)-5-heptylpyrrolidine 
• 4762-26-9 hexyltriphenylphosphonium bromide 
• 109-72-8 n-butyllithium 
• 1179523-35-3 C₁₁H₂₁N 
• 131403-21-9 (2S,5R)-1-benzyloxycarbony-2-butyl-5-(hydroxymethyl)pyrrolidine 
• 131403-22-0 (2S,5R)-2-Butyl-5-formyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 105147-72-6 1-((2S,3aR,6R)-2-Ethyl-hexahydro-pyrrolo[1,2-b]isoxazol-6-yl)-heptan-2-ol 
• 105147-70-4 (2R,3aR)-2-Pentyl-hexahydro-pyrrolo[1,2-b]isoxazole 
• 592-76-7 1-Heptene 

Downstream Products

• 112020-14-1 (+)-(S)-trans-2-heptyl-5-butyl-1-benzyl pyrrolidine 
• 105147-82-8 (2S,5R)-1-Benzyl-2-butyl-5-heptyl-pyrrolidine 
• 95587-13-6 (+)-(S)-trans-2-heptyl-5-butyl-1-phenyl sulfonyl pyrrolidine 
• 105147-76-0 ((2S,5S)-2-Butyl-5-heptyl-pyrrolidin-1-yl)-phenyl-methanone 
• 111964-20-6 (S)-1-((2S,5S)-2-Butyl-5-heptyl-pyrrolidin-1-yl)-3,3,3-trifluoro-2-methoxy-2-phenyl-propan-1-one 

Relevant academic research and scientific papers

Enantioselective syntheses of 2-substituted pyrrolidines from allylamines by domino hydroformylation-condensation: Short syntheses of (S)-nicotine and the alkaloid 225C

Short routes to chiral 2-substituted pyrrolidines based on rhodium-catalyzed hydroformylations of allylamines and their N-alkyl and N-acyl derivatives, which were prepared by asymmetric allylic substitutions, are described. The outcome of the hydroformyla

(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.

Organolanthanide-catalyzed hydroamination/cyclization. Efficient allene- based transformations for the syntheses of naturally occurring alkaloids

The total syntheses of the pyrrolidine alkaloid (+)-197B (1) and pyrrolizidine alkaloid (+)-xenovenine (2) are described. The strategy involves enantioselective syntheses of the aminoallene, (5S,8S)-5-amino- trideca-8,9-diene (3), and the aminoallene-alkene, (5S)-5-amino-pentadeca- 1,8,9-triene (4), which then undergo regio- and stereoselective cyclohydroamination catalyzed by the organolanthanide precatalysts Cp'2LnCH(TMS)2 and Me2SiCp''((t)BuN)LnN(TMS)2 (Cp' = η5-Me5C5; Cp'' = η5-Me4C5; Ln = lanthanide; TMS = Me3Si). These reactive organolanthanide complexes efficiently mediate highly diastereoselective intramolecular hydroamination/cyclization (IHC) reactions under mild conditions. The turnover-limiting step in these catalytic cycles is proposed to be intramolecular insertion into the Ln-N bond of the proximal allenic C=C linkage, followed by rapid protonolytic cleavage of the resulting Ln-C bond. The rate and selectivity of the insertion process is highly sensitive to the steric demands of the substrate.

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.

ASYMMETRIC SYNTHESIS XII: STEREOCONTROLLED ELECTROPHILIC-NUCLEOPHILIC α,α'-SUBSTITUTION OF THE PYRROLIDINE RING.

The synthesis of 2-cyano-5-oxazolopyrrolidine 3, a chiral pyrrolidine synthon, is described.Conditions were established that permitted sequential chemoselective reactions at the C-2 aminonitrile (electrophilic substitution) and at the C-5 aminoether (nucl

ASYMMETRIC SYNTHESIS X : A CHIRAL PYRROLIDINE SYNTHON FOR A NEW APPROACH TO THE SYNTHESIS OF ALKALOIDS

The synthesis of chiral 2-cyano-5-oxazolopyrrolidine 3 is reported.The synthesis of the optically pure ant venom alkaloid, (+)-(S)-trans-2-heptyl-5-butyl-pyrrolidine 7, has been achieved from 3.

THE α,α'-DIALKYLATION OF CYCLIC AMINES. THE SYNTHESIS OF SOLENOPSIS ANT VENOMS.

A trans-α,α'-dialkylation of cyclic amines has been investigated through the use of nitrone methodology.This procedure has been utilized in the synthesis of Solenopsis 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.