90290-05-4

Basic information

• Product Name: (R,R)-(-)-2,5-BIS(METHOXYMETHYL)-PYRROLIDINE
• Synonyms: (R,R)-(-)-2,5-BIS(METHOXYMETHYL)-PYRROLIDINE;(-)-2,3,4,5-Tetradeoxy-2,5-imino-1-O,6-O-dimethyl-L-threo-hexitol;(2R)-2β,5α-Bis(methoxymethyl)pyrrolidine;(2R,5R)-2,5-Bis(methoxymethyl)pyrrolidine;[2R,5R,(-)]-2,5-Bis(methoxymethyl)pyrrolidine;2β,5α-Bis(methoxymethyl)pyrrolidine;(R,R)-(-)-2,5-Bis(methoxymethyl)pyrrolidine,96%
• CAS NO: 90290-05-4
• Molecular Formula: C₈H₁₇NO₂
• Molecular Weight: 159.23
• Mol File: 90290-05-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 106-108°C/18mm
• Flash Point: 106-108°C/18mm
• Appearance: /
• Density: 1.0469 (rough estimate)
• Vapor Pressure: 0.382mmHg at 25°C
• Refractive Index: 1.447-1.449
• Storage Temp.: Refrigerator (+4°C)
• CAS DataBase Reference: (R,R)-(-)-2,5-BIS(METHOXYMETHYL)-PYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R,R)-(-)-2,5-BIS(METHOXYMETHYL)-PYRROLIDINE(90290-05-4)
• EPA Substance Registry System: (R,R)-(-)-2,5-BIS(METHOXYMETHYL)-PYRROLIDINE(90290-05-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• Hazardous Substances Data: 90290-05-4(Hazardous Substances Data)

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

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

Downstream Products

• 90290-12-3 1-((2R,5R)-2,5-Bis-methoxymethyl-pyrrolidin-1-yl)-3-phenyl-propan-1-one 
• 188030-75-3 N,N'-(diselenodi-2,1-phenylenemethylene)bis[(2R,5R)-bis(methoxymethyl)pyrrolidine] 
• 194607-35-7 (2R,5R)-1-Cyclohex-1-enyl-2,5-bis-methoxymethyl-pyrrolidine 
• 851512-46-4 (2R,5R)-1-((2'S)-3'-acetylthio-2'-methylpropanoyl)-2,5-bis(methoxymethyl)pyrrolidine 
• 292047-63-3 (R)-3,4-dihydro-2,5-bis(methoxymethyl)-2-phenyl-2H-pyrrole 1-oxide 
• 292047-61-1 (2R,5R)-1-hydroxy-2,5-bis(methoxymethyl)-2-phenylpyrrolidine 

Relevant articles and documents

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 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

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.