128542-75-6

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-2-BromoMethyl-pyrrolidine-1-carboxylic acid tert-butyl ester is used as a key intermediate for the preparation of pyrrolidine-based drugs. Its unique structure allows for the development of antiviral and antihypertensive medications, making it an essential component in the pharmaceutical industry.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-2-BromoMethyl-pyrrolidine-1-carboxylic acid tert-butyl ester serves as a valuable building block. Its bromomethyl group facilitates further functionalization, enabling the creation of a wide range of organic compounds for various applications.
Used in Medicinal Chemistry:
(S)-2-BromoMethyl-pyrrolidine-1-carboxylic acid tert-butyl ester is utilized in medicinal chemistry for the design and synthesis of novel therapeutic agents. Its versatility and reactivity make it a preferred choice for researchers working on the development of new drugs with improved efficacy and safety profiles.

Upstream product

• 132482-09-8 tert-butyl (2S)-2-{[(methylsulfonyl)oxy]methyl}-pyrrolidine-1-carboxylate 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 86661-32-7 (S)-tert-butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate 
• 147-85-3 L-proline 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 

Downstream Products

• 73236-85-8 (S)-2-<(acetylthio)methyl>-1-<(tert-butyloxy)carbonyl>pyrrolidine 
• 204137-96-2 (S)-tert-butyl 2-{[4-(trifluoromethyl)phenyl]sulfanylmethyl}-pyrrolidine-1-carboxylate 
• 1190207-25-0 (S)-N-tert-butoxycarbonyl-2-[bis(2-methylphenyl)phosphinomethyl]pyrrolidine 
• 1352662-96-4 adamantan-1-yl-((S)-1-{2-[(dicyclohexylphosphino)methyl]pyrrolidin-1-yl})-methanone 
• 1352662-97-5 (S)-1-{2-[(diphenylphosphino)methyl]pyrrolidin-1-yl}-2,2,2-triphenylethanone 
• 1352662-99-7 (S)-1-{2-[(di-tert-butylphosphino)methyl]pyrrolidin-1-yl}-2,2,2-triphenylethanone 
• 1352663-01-4 (S)-1-{2-[(dicyclohexylphosphino)methyl]pyrrolidin-1-yl}-2,2,2-triphenylethanone 
• 1352663-05-8 (S)-N-(adamantan-1-yl)-2-[(dicyclohexylphosphino)methyl]pyrrolidine-1-carboxamide 
• 1352663-07-0 (S)-2-[(di-tert-butylphosphino)methyl]-N-mesitylpyrrolidine-1-carboxamide 
• 1352663-09-2 (S)-2-[(dicyclohexylphosphino)methyl]-N-mesitylpyrrolidine-1-carboxamide 
• 1352663-10-5 (S)-2-[(diphenylphosphino)methyl]-N-tritylpyrrolidine-1-carboxamide 
• 1352663-12-7 (S)-2-[(di-tert-butylphosphino)methyl]-N-tritylpyrrolidine-1-carboxamide 
• 1352663-14-9 (S)-2-[(dicyclohexylphosphino)methyl]-N-tritylpyrrolidine-1-carboxamide 
• 1352663-15-0 (S)-2-[(di-o-tolylphosphino)methyl]-N,N-diisopropylpyrrolidine-1-carboxamide 

Relevant academic research and scientific papers

Prolinamides of Aminouracils, Organocatalyst Modifiable by Complementary Modules

We report the synthesis and evaluation of prolinamide organocatalysts that incorporate aminouracils. The features of these catalysts are enhanced NH acidity of the amide because of the electron-withdrawing nature of the heterocycle, an additional hydrogen-bond donor at the α or β positions of this functional group (using 6-aminouracil or 5,6-diaminouracil respectively), and it can be recovered due to its low solubility and used again without decreasing the enantioselectivity. A unique feature of these systems is the self-assembly capability with complementary modules by Watson–Crick interactions. These supramolecular adducts behave differently from the catalyst alone, some of them have lower performance but others improve the selectivity of the product. Therefore, this approach avoids the synthesis of many catalysts.

Trisubstituted Pyridinylimidazoles as Potent Inhibitors of the Clinically Resistant L858R/T790M/C797S EGFR Mutant: Targeting of Both Hydrophobic Regions and the Phosphate Binding Site

Inhibition of the epidermal growth factor receptor represents one of the most promising strategies in the treatment of lung cancer. Acquired resistance compromises the clinical efficacy of EGFR inhibitors during long-term treatment. The recently discovered EGFR-C797S mutation causes resistance against third-generation EGFR inhibitors. Here we present a rational approach based on extending the inhibition profile of a p38 MAP kinase inhibitor toward mutant EGFR inhibition. We used a privileged scaffold with proven cellular potency as well as in vivo efficacy and low toxicity. Guided by molecular modeling, we synthesized and studied the structure-activity relationship of 40 compounds against clinically relevant EGFR mutants. We successfully improved the cellular EGFR inhibition down to the low nanomolar range with covalently binding inhibitors against a gefitinib resistant T790M mutant cell line. We identified additional noncovalent interactions, which allowed us to develop metabolically stable inhibitors with high activities against the osimertinib resistant L858R/T790M/C797S mutant.

Sequential deprotectionecyclisation reaction: Stereoselective synthesis of azabicyclic β-enamino ester derivatives and (-) indolizidine 209D

This paper describes a new strategy for the stereoselective synthesis of pyrrolizidine and indolizidine based enamino esters and their acyl derivatives from L-proline. The key reaction in this process involves deprotection followed by ring closure of cyclic N-Boc amino-β-ketoesters. Also, the synthesis of 5R,9R- (-)-indolizidine 209D has been accomplished using this protocol.

Chiral quaternary alkylammonium ionic liquid [Pro-dabco][BF4]: As a recyclable and highly efficient organocatalyst for asymmetric Michael addition reactions

A novel series of chiral quaternary ammonium ionic liquids have been synthesized and shown to be very effective catalysts for the asymmetric Michael addition reactions of ketones and aldehydes to nitroolefins with excellent yields (up to 100%), diastereos

QUINOLINE AND QUINOXALINE DERIVATIVES AS INHIBITORS OF KINASE ENZYMATIC ACTIVITY

Compounds of formula (IA) or (IB), are inhibitors of aurora kinase activity: Formula (IA), (IB) wherein -L1Y1-[CH2]z- is a linker radical wherein Y1, L1 and z are as defined in the claims; R6 is C1-C4alkoxy, hydrogen or halo; W represents a bond, -CH2-, -O-, -S-, -S(=O)2-, or -NR5- where R5 is hydrogen or C1-C4 alkyl; Q is =N-, =CH- or =C(X1)- wherein X1 is cyano, cyclopropyl or halo; linker radicals L2 are as defined in the claims; R is a radical of formula (X) or (Y): wherein R1 is a carboxylic acid group (-COOH), or an ester group which is hydrolysable by one or more intracellular carboxylesterase enzymes to a carboxylic acid group; R4 is hydrogen; or optionally substituted C1-C6 alkyl, C3-C7 cycloalkyl, aryl, aryl(C1-C6 alkyl)-, heteroaryl, heteroaryl(C1-C6 alkyl)-, -(C=O)R3, -(C=O)OR3, or -(C=O)NR3 wherein R3 is hydrogen or optionally substituted (C1-C6)alkyl, C3-C7 cycloalkyl, aryl, aryl(C1-C6 alkyl)-, heteroaryl, or heteroaryl(C1-C6 alkyl)-; R41 is hydrogen or optionally substituted C1-C6 alkyl; and D is a monocyclic heterocyclic ring of 5 or 6 ring atoms.

11β LONG-CHAIN SUBSTITUTED ESTRATRIENES, METHOD FOR THEIR PRODUCTION, PHARMACEUTICAL PREPARATIONS CONTAINING SAID 11β LONG-CHAIN SUBSTITUTED ESTATRIENES, AND THEIR USE FOR PRODUCING MEDICAMENTS

This invention describes a 11β-long-chain-substituted estratriene of general formula (I), in which R11is a long-chain radical that has a nitrogen atom and optionally a sulfur atom, which in addition can be functionalized in the terminal positio

An efficient route to alkyl chlorides from alcohols using the complex TCT/DMF

(formula presented) Efficient conversion of alcohols and β-amino alcohols to the corresponding chlorides (and bromides) can be carried out at room temperature in methylene chloride, using 2,4,6-trichloro[1,3,5]triazine and N,N-dimethyl formamide. This procedure can also be applied to optically active carbinols.

Homodimeric and heterodimeric bis(amino thiol) oxometal complexes with rhenium(V) and technetium(V). Control of heterodimeric complex formation and an approach to metal complexes that mimic steroid hormones

We have investigated the possibility of preparing complexes of rhenium and technetium whose shape resembles that of ligands for steroid receptors. The general structure of N2S2 complexes of oxorhenium(V) and oxotechnetium(V) is such that they could replace the BC ring system of steroid, thereby generating a metal complex system with considerable size and shape similarity to a steroid. Such a metal-integrated steroid-shaped complex can be constructed as a heterodimer of two different amino thiols; complexes of rhenium and technetium with such heterodimeric bis-bidentate structure have not been systematically studied. In this investigation, we have shown that complexes of this nature form readily when appropriate metal precursors are combined with a mixture of amino thiols. In the systems we have studied, heterodimeric complex formation is preferred over homodimeric complex formation, and in one system where we were able to obtain an X-ray crystal structure, this oxorhenium heterodimer had the desired trans geometry. These rhenium and technetium-99m complexes are reasonably stable toward ligand exchange; they can be readily purified by chromatography under appropriate conditions, and the one technetium-99m complex studied in vivo shows some persistence in blood and gives good initial uptake in several tissues. The convenient and selective formation of such bis-bidentate heterodimeric complexes suggests that the development of metal-integrated complexes that resemble ligands for receptors may be possible.

An enantioselective michael addition of soft nucleophiles to prochiral enone catalyzed by (2-Pyrrolidyl)alkyl ammonium hydroxide

(S)-N-(2-Pyrrolidylmethyl)-N,N,N-trimethylammonium hydoxide catalyzes the asymmetric Michael addition of soft nucleophiles to enones with moderate to high enantiomeric excess through ion-pair rather than steric control.