643759-58-4

Usage

Uses

Used in Pharmaceutical Synthesis:
1-Boc-2,5-dihydro-3-Methyl-1H-pyrrole is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the formation of complex molecular structures. The Boc protecting group allows for selective reactions to occur without affecting the amine functionality, which is vital for the development of new drugs with specific therapeutic properties.
Used in Organic Chemistry:
In the field of organic chemistry, 1-Boc-2,5-dihydro-3-Methyl-1H-pyrrole is utilized as a versatile building block for the creation of a wide range of organic molecules. Its structural features and the protective Boc group enable chemists to carry out intricate synthetic routes, leading to the production of advanced organic compounds with diverse applications.
Used in Peptide Synthesis:
1-Boc-2,5-dihydro-3-Methyl-1H-pyrrole is employed as a component in peptide synthesis, where the Boc group plays a critical role in protecting the amine group of proline during the assembly of peptide chains. This protection allows for the stepwise addition of amino acids, facilitating the synthesis of peptides with specific sequences and functions.
Used in Research and Development:
In research and development settings, 1-Boc-2,5-dihydro-3-Methyl-1H-pyrrole is used as a valuable tool for studying the properties and reactivity of proline-containing compounds. Its presence in various chemical reactions provides insights into the mechanisms and outcomes of organic synthesis, contributing to the advancement of chemical knowledge and innovation.

Upstream product

• 897445-49-7 2,2,2-trifluoro-1-(3-methyl-2,5-dihydro-pyrrol-1-yl)-ethanone 
• 24424-99-5 di-tert-butyl dicarbonate 
• 78888-18-3 N-tert-butoxycarbonylprop-2-en-1-amine 
• 643759-57-3 tert-butyl allyl(2-methylallyl)carbamate 

Downstream Products

• 897445-50-0 tert-butyl 1-methyl-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate 
• 127073-77-2 1-Benzyl-3-methyl-2,5-dihydro-1H-pyrrole 

Relevant academic research and scientific papers

Fast olefin metathesis at low catalyst loading

Reactions of the Grubbs 3rd generation complexes [RuCl2(NHC) (Ind)(Py)] (N-heterocyclic carbene (NHC)=1,3-bis(2,4,6- trimethylphenylimidazolin)-2-ylidene (SIMes), 1,3-bis(2,6- diisopropylphenylimidazolin)-2-ylidene (SIPr), or 1,3-bis(2,6- diisopropylphenylimidazol)-2-ylidene (IPr); Ind=3-phenylindenylid-1-ene, Py=pyridine) with 2-ethenyl-N-alkylaniline (alkyl=Me, Et) result in the formation of the new N-Grubbs-Hoveyda-type complexes 5 (NHC=SIMes, alkyl=Me), 6 (SIMes, Et), 7 (IPr, Me), 8 (SIPr, Me), and 9 (SIPr, Et) with N-chelating benzylidene ligands in yields of 50-75 %. Compared to their respective, conventional, O-Grubbs-Hoveyda complexes, the new complexes are characterized by fast catalyst activation, which translates into fast and efficient ring-closing metathesis (RCM) reactivity. Catalyst loadings of 15-150 ppm (0.0015-0.015 mol %) are sufficient for the conversion of a wide range of diolefinic substrates into the respective RCM products after 15 min at 50 °C in toluene; compounds 8 and 9 are the most catalytically active complexes. The use of complex 8 in RCM reactions enables the formation of N-protected 2,5-dihydropyrroles with turnover numbers (TONs) of up to 58 000 and turnover frequencies (TOFs) of up to 232 000 h-1; the use of the N-protected 1,2,3,6-tetrahydropyridines proceeds with TONs of up to 37 000 and TOFs of up to 147 000 h-1; and the use of the N-protected 2,3,6,7-tetrahydroazepines proceeds with TONs of up to 19 000 and TOFs of up to 76 000 h-1, with yields for these reactions ranging from 83-92 %. The tortoise and the hare: The use of diphenylalkylamino-based instead of phenyldialkylamino-based styrenes (see figure) leads to rapidly initiating precatalysts that enable very fast ring-closing metathesis reactions with turnover numbers of up to 58 000 and turnover frequencies of up to 232 000 h-1. Copyright

Low catalyst loadings in olefin metathesis: Synthesis of nitrogen heterocycles by ring-closing metathesis

(Chemical Equetion Presentation) A series of ruthenium catalysts have been screened under ring-closing metathesis (RCM) conditions to produce five-, six-, and seven-membered carbamate-protected cyclic amines. Many of these catalysts demonstrated excellent RCM activity and yields with as low as 500 ppm catalyst loadings. RCM of the five-membered carbamate series could be run neat, the six-membered carbamate series could be run at 1.0 M, and the seven-membered carbamate series worked best at 0.2-0.05 M.

COMPOUNDS USEFUL AS CHEMOKINE RECEPTOR ANTAGONISTS

The present invention relates to compounds useful as Chemokine Receptor antagonists. Compounds of general formula I are provided: or pharmaceutically acceptable salts thereof. The invention also provides pharmaceutically acceptable compositions comprising said compounds and methods of using the compounds and compositions for the inhibition of Chemokine Receptors and also for the treatment of various diseases, conditions, or disorders, including acute or chronic inflammatory disease, cancer or osteolytic bone disorders.

Organolithium-induced synthesis of acyclic unsaturated amino alcohols from epoxides of dihydropyrroles and tetrahydropyridines

The alkylative double ring-opening of Bus-protected 2,5-dihydropyrrole epoxides 13 and 29 with organolithiums to give 3-substituted 1-aminobut-3-en-2-ols 13-19 and 30-32 are described. Bus-protected tetrahydropyridine epoxide 38 reacts with organolithiums to give 4-substituted 1-aminobut-4-en-3-ols 39 and tetrahydropyridinol 40.