71732-80-4

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 629-04-9 1-Bromoheptane 
• 195299-15-1 2-cyano-5-oxazolopyrrolidine 
• 109-72-8 n-butyllithium 
• 1179523-35-3 C₁₁H₂₁N 
• 3452-09-3 1-nonyne 
• 3637-16-9 5-oxododecanoic acid 
• 6093-96-5 methyl 5-oxo-dodecanoate 
• 105147-77-1 1-((3aR,6R)-2-Vinyl-hexahydro-pyrrolo[1,2-b]isoxazol-6-yl)-heptan-2-ol 
• 111964-19-3 (R)-2-((2S,5S)-2-Butyl-5-heptyl-pyrrolidin-1-yl)-2-phenyl-ethanol 
• 62992-46-5 1-(tetrahydropyranyloxy)-4-pentyn 
• 592-76-7 1-Heptene 
• 95587-18-1 (2R)-cis-5-butyl-2-heptyl-1-(phenylsulfonyl)pyrrolidine 
• 95513-49-8 (2S)-cis-1-benzyl-5-butylproline tert-butyl ester 

Downstream Products

• 112020-14-1 (+)-(S)-trans-2-heptyl-5-butyl-1-benzyl pyrrolidine 
• 129446-24-8 (2R-trans)-2-butyl-5-heptyl-1-phenylsulfonylpyrrolidine 
• 112020-16-3 cis-2-heptyl-5-butyl-1-benzyl pyrrolidine 
• 105147-76-0 ((2R,5S)-2-Butyl-5-heptyl-pyrrolidin-1-yl)-phenyl-methanone 

Relevant academic research and scientific papers

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.

Reaction of Nitrogen-Radicals with Organometallics Under Ni-Catalysis: N-Arylations and Amino-Functionalization Cascades

Herein, we report a strategy for the generation of nitrogen-radicals by ground-state single electron transfer with organyl–NiI species. Depending on the philicity of the N-radical, two types of processes have been developed. In the case of nucleophilic aminyl radicals direct N-arylation with aryl organozinc, organoboron, and organosilicon reagents was achieved. In the case of electrophilic amidyl radicals, cascade processes involving intramolecular cyclization, followed by reaction with both aryl and alkyl organometallics have been developed. The N-cyclization–alkylation cascade introduces a novel retrosynthetic disconnection for the assembly of substituted lactams and pyrrolidines with its potential demonstrated in the short total synthesis of four venom alkaloids.

Redox-Triggered α-C-H Functionalization of Pyrrolidines: Synthesis of Unsymmetrically 2,5-Disubstituted Pyrrolidines

By using o-benzoquinone as an internal oxidant, the regio- and diastereoselective functionalization of the secondary over the tertiary α-C-H bond of 2-substituted pyrrolidines is first realized. Subsequent intermolecular addition of a nucleophile to the g

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

Efficient carboazidation of alkenes using a radical desulfonylative azide transfer process

The radical-mediated carboazidation of terminal alkenes using electrophilic alkanesulfonyl azides is reported. A single reagent delivers the necessary electrophilic alkyl radical as well as the azido group, and good yields are obtained by using a moderate excess of the carboazidating reagent (1.5-2 equiv). Interestingly, in addition to the starting sulfonyl azide, this method requires only the use of a radical initiator, di-tert-butyldiazene. In terms of atom economy, this azide transfer reaction is close to ideal, as SO2 (1 equiv) is the only side product. The synthetic potential of this process has been demonstrated by a formal synthesis of the alkaloid lepadiformine C.

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

Asymmetric synthesis of polyfunctionalized pyrrolidines from sulfinimine-derived pyrrolidine 2-phosphonates. Synthesis of pyrrolidine 225C

The Horner-Wadsworth-Emmons reaction of aldehydes with sulfinimine-derived 3-oxo pyrrolidine phosphonates represents a new method for the asymmetric synthesis of ring-functionalized cis-2,5-disubstituted 3-oxo pyrrolidines.

(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.

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).