90290-05-4

Usage

Chemical Properties

clear colorless to light yellow liquid

InChI:InChI=1/C8H17NO2/c1-10-5-7-3-4-8(9-7)6-11-2/h7-9H,3-6H2,1-2H3/p+1/t7-,8-/m1/s1

Upstream product

• 90290-04-3 trans-N-benzyl-2,5-bis(ethoxycarbonyl)pyrrolidine 
• 74-88-4 methyl iodide 
• 93713-36-1 1-Benzyl-[(2R,5R)-2,5-bis(hydroxymethyl)]pyrrolidine 
• 148773-73-3 (2R,5R)-1-<(S)-1-Phenylethyl>-2,5-bis(methoxymethyl)pyrrolidine 
• 148773-69-7 (2S,5S)-1-<(S)-1-Phenylethyl>-2,5-bis(methoxymethyl)pyrrolidine 
• 145472-51-1 (2S,5S)-2,5-Bis-methoxymethyl-1-(toluene-4-sulfonyl)-pyrrolidine 
• 1445166-99-3 trans-N-benzyl-2,5-bis(methoxymethyl)pyrrolidine 

Downstream Products

• 90290-12-3 1-((2R,5R)-2,5-Bis-methoxymethyl-pyrrolidin-1-yl)-3-phenyl-propan-1-one 
• 851512-46-4 (2R,5R)-1-((2'S)-3'-acetylthio-2'-methylpropanoyl)-2,5-bis(methoxymethyl)pyrrolidine 
• 90290-27-0 (R)-3-Benzyloxy-1-((2R,5R)-2,5-bis-methoxymethyl-pyrrolidin-1-yl)-2-methyl-propan-1-one 
• 90290-22-5 (R)-1-((2R,5R)-2,5-Bis-methoxymethyl-pyrrolidin-1-yl)-2-methyl-3-phenyl-propan-1-one 
• 90290-23-6 (S)-1-((2R,5R)-2,5-Bis-methoxymethyl-pyrrolidin-1-yl)-2-methyl-3-phenyl-propan-1-one 
• 194607-35-7 (2R,5R)-1-Cyclohex-1-enyl-2,5-bis-methoxymethyl-pyrrolidine 
• 188030-75-3 N,N'-(diselenodi-2,1-phenylenemethylene)bis[(2R,5R)-bis(methoxymethyl)pyrrolidine] 

Relevant academic research and scientific papers

Influence of 4- or 5-substituents on the pyrrolidine ring of 5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin derivatives on their inhibitory activities towards caspases-3 and -7 Dedicated to Professor Dr. Ernst-Ulrich Würthwein on the occasion of his 65th birthday

A series of new 4- or 5-substituted pyrrolidine derivatives of 5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin bearing additional n-butyl or 4-fluorobutyl groups at the isatin nitrogen were prepared and their inhibitory activities have been tested against caspases-3 and -7, which are known to participate in the execution of the programmed cell death, called apoptosis. Several analogues fluorinated at the 4-position of the pyrrolidine ring were also synthesized since such inhibitors might be developed as 18F-radiotracers for molecular imaging of activated caspases in vivo by PET. Enantiomerically pure diastereomeric 4-fluoropyrrolidinyl derivatives inhibited the enzymes in the nanomolar scale, i.e.100-1000 times more efficient than the corresponding 4-methoxy analogues. The 4,4-difluorinated compound showed the best result with IC50 = 362 nM and 178 nM for the aforementioned caspases. In contrast, the 4-methoxy and 4-trifluoromethyl analogues exhibited less inhibition potencies for the enzymes in the μM scale, whereas all 4-OPEG4 (PEG4 = tetraethyleneglycol) and 5-methoxymethyl derivatives were inactive.

A straightforward synthesis of enantiomerically pure trans-2,5-bis(alkyloxymethyl) pyrrolidines by 1,3-dipolar cycloaddition reactions of azomethine ylides

A new efficient method for the stereoselective preparation of trans-2,5-bis(alkyloxymethyl)pyrrolidines (7) using easily available starting materials is described. The main step of this synthesis is the stereoselective formation of the pyrrolidine ring by

A convenient synthesis of enantiomeric pairs of 2,5-disubstituted pyrrolidines of C2-symmetry

By the use of (-)-1-phenylethylamine as a chiral auxiliary, three diastereomeric isomers of 2,5-bis(methoxycarbonyl)pyrrolidine derivatives are prepared from dimethyl rac-2,5-dibromadipate and separted by crystallization and chromatographic fractionation

Carbon-Carbon Bond Formation via N-Tosyliminium Ions

Addition of carbon nucleophiles to cyclic N-tosyliminium ions, derived from α-hydroxy and α-methoxy tosylamides (5a,b and 6a,b, respectively) is described.In general, good to excellent yields were obtained when allyltrimethylsilane, 1-t-butyldimethylsilyl

ASYMMETRIC ALKYLATION OF CARBOXYAMIDES BY USING trans-2,5-DISUBSTITUTED PYRROLIDINES AS CHIRAL AUXILIARIES

trans-2,5-Bis(methoxymethyl)- and trans-2,5-bis(methoxymethoxymethyl)pyrrolidines proved to be excellent chiral auxiliaries for the asymmetric alkylation of the corresponding carboxyamide enolates giving good chemical yield and high stereoselectivity (invariably over 95percent de), with remarkable flexibility to substrates and reaction conditions.