176324-60-0

Usage

Uses

Used in Pharmaceutical Industry:
1-Pyrrolidinecarboxylic acid, 2-ethenyl-, 1,1-dimethylethyl ester is used as a reagent in organic synthesis for its ability to react with various nucleophiles, making it an important building block in the production of complex organic molecules.
Used in Drug Synthesis:
N-Boc-pyrrole is used as a precursor in the synthesis of drugs and other biologically active compounds, contributing to the development of new pharmaceuticals and therapeutic agents.
Used in Organic Chemistry Research:
1-Pyrrolidinecarboxylic acid, 2-ethenyl-, 1,1-dimethylethyl ester is employed in organic chemistry research to explore its reactivity and potential applications in the synthesis of novel compounds and materials.

Upstream product

• 59378-82-4 N-(tert-butoxycarbonyl)pyrrolidine-2-carboxaldehyde 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 69610-41-9 Boc-L-Pro-H 
• 821-77-2 5-hexenylazide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1112-56-7 tetravinyltin (IV) 
• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 18922-06-0 hex-5-enyl 4-methylbenzenesulfonate 
• 821-41-0 5-Hexen-1-ol 

Downstream Products

• 107131-61-3 2-vinylpyrrolidine 
• 170491-62-0 2-(2-oxoethyl)pyrrolidine-1-carboxylic acid tert-butyl ester 
• 64871-53-0 1-(N-benzylamino)-2-vinylpyrrolidine 
• 125348-98-3 2-vinylpyrrolidine hydrochloride 

Relevant academic research and scientific papers

Iron-Phosphine Complex-Catalyzed Intramolecular C(sp3)-H Amination of Azides

Fe(II)-phosphine complex [Fe(dpbz)]Cl2 was demonstrated to be effective for the intramolecular C(sp3)-H amination of organic azides. This catalyst exhibited a high catalytic capacity for the transformations from α-azido amides to imi

Metal-organic frameworks containing nitrogen-donor ligands for efficient catalytic organic transformations

Metal-organic framework (MOFs) compositions based on nitrogen donor-based organic bridging ligands, including ligands based on 1,3-diketimine (NacNac), bipyridines and salicylaldimine, were synthesized and then post-synthetically metalated with metal precursors, such as complexes of first row transition metals. Metal complexes of the organic bridging ligands could also be directly incorporated into the MOFs. The MOFs provide a versatile family of recyclable and reusable single-site solid catalysts for catalyzing a variety of asymmetric organic transformations. The solid catalysts can also be integrated into a flow reactor or a supercritical fluid reactor.

An Effective [FeIII(TF4DMAP)Cl] Catalyst for C-H Bond Amination with Aryl and Alkyl Azides

[FeIII(TF4DMAP)Cl] can efficiently catalyze intermolecular sp3 C-H amination using aryl azides and intramolecular sp3 C-H amination of alkyl azides in moderate-to-high product yields. At catalyst loading down to 1 mol %, the reactions display high chemo- and regioselectivity with broad substrate scope and are effective for late-stage functionalization of complex natural/bioactive molecules.

N-Heterocyclic Carbene Iron(III) Porphyrin-Catalyzed Intramolecular C(sp3)–H Amination of Alkyl Azides

Metal-catalyzed intramolecular C?H amination of alkyl azides constitutes an appealing approach to alicyclic amines; challenges remain in broadening substrate scope, enhancing regioselectivity, and applying the method to natural product synthesis. Herein we report an iron(III) porphyrin bearing axial N-heterocyclic carbene ligands which catalyzes the intramolecular C(sp3)–H amination of a wide variety of alkyl azides under microwave-assisted and thermal conditions, resulting in selective amination of tertiary, benzylic, allylic, secondary, and primary C?H bonds with up to 95 % yield. 14 out of 17 substrates were cyclized selectively at C4 to give pyrrolidines. The regioselectivity at C4 or C5 could be tuned by modifying the reactivity of the C5–H bond. Mechanistic studies revealed a concerted or a fast re-bound mechanism for the amination reaction. The reaction has been applied to the syntheses of tropane, nicotine, cis-octahydroindole, and leelamine derivatives.

Stereocontrolled Total Synthesis of (?)-Stemaphylline

Homologation of readily available α-boryl pyrrolidines with metal carbenoids is especially challenging even when good leaving groups (Cl?) are employed. By performing a solvent switch from Et2O to CHCl3, efficient 1,2-metalate rearrangement of the intermediate boronate occurs with both halide and ester leaving groups. The methodology was used in the total synthesis of the Stemona alkaloid (?)-stemaphylline in just 11 steps (longest linear sequence), with high stereocontrol (>20:1 d.r.) and 11 % overall yield. The synthesis also features a late-stage lithiation–borylation reaction with a tertiary amine containing carbenoid.

Catalytic Synthesis of N-Heterocycles via Direct C(sp3)-H Amination Using an Air-Stable Iron(III) Species with a Redox-Active Ligand

Coordination of FeCl3 to the redox-active pyridine-aminophenol ligand NNOH2 in the presence of base and under aerobic conditions generates FeCl2(NNOISQ) (1), featuring high-spin FeIII and an NNOISQ radical ligand. The complex has an overall S = 2 spin state, as deduced from experimental and computational data. The ligand-centered radical couples antiferromagnetically with the Fe center. Readily available, well-defined, and air-stable 1 catalyzes the challenging intramolecular direct C(sp3)-H amination of unactivated organic azides to generate a range of saturated N-heterocycles with the highest turnover number (TON) (1 mol% of 1, 12 h, TON = 62; 0.1 mol% of 1, 7 days, TON = 620) reported to date. The catalyst is easily recycled without noticeable loss of catalytic activity. A detailed kinetic study for C(sp3)-H amination of 1-azido-4-phenylbutane (S1) revealed zero order in the azide substrate and first order in both the catalyst and Boc2O. A cationic iron complex, generated from the neutral precatalyst upon reaction with Boc2O, is proposed as the catalytically active species.

Metal-organic layers stabilize earth-abundant metal-terpyridine diradical complexes for catalytic C-H activation

We report the synthesis of a terpyridine-based metal-organic layer (TPY-MOL) and its metalation with CoCl2 and FeBr2 to afford CoCl2·TPY-MOL and FeBr2·TPY-MOL, respectively. Upon activation with NaEt3

One-Pot Three-Component Synthesis of Vicinal Diamines via In Situ Aminal Formation and Carboamination

A synthesis of vicinal diamines via in situ aminal formation and carboamination of allyl amines is reported. Employing highly electron-poor trifluoromethyl aldimines in their stable hemiaminal form was key to enable both a fast and complete aminal formation as well as the palladium-catalyzed carboamination step. The conditions developed allow the introduction of a wide variety of alkynyl, vinyl, aryl, and hetereoaryl groups with complete regioselectivity and high diastereoselectivity. The reaction exhibits a high functional-group tolerance. Importantly, either nitrogen atom of the imidazolidine products can be selectively deprotected, while removal of the aminal tether can be achieved in a single step under mild conditions to reveal the free diamine. We expect that this work will promote the further use of mixed aminal tethers in organic synthesis.

NOVEL KINASE INHIBITORS

The present invention provides derivatives of thiazolylamino-substituted heterocycles. These compounds are inhibitors of kinases, including compounds that show antiproliferative activity against cells, including against tumor cells, and are useful in the treatment of diseases including cancer.

SYNTHESIS OF ACYCLIC AND CYCLIC AMINES USING IRON-CATALYZED NITRENE GROUP TRANSFER

The present invention provides novel synthetic methods for making acyclic secondary amines by reacting an azide with a compound bearing one or more C-H groups, catalyzed by a FeII-dipyrromethene complex. The acyclic secondary amines are thought