62617-70-3

Basic information

• Product Name: (2R,5R)-(-)-TRANS-2,5-DIMETHYLPYRROLIDINE
• Synonyms: (2R,5R)-(-)-TRANS-2,5-DIMETHYLPYRROLIDINE;Pyrrolidine, 2,5-dimethyl-, (2R,5R)-
• CAS NO: 62617-70-3
• Molecular Formula: C₆H₁₃N
• Molecular Weight: 99.17
• Product Categories: Chiral Building Blocks;Heterocyclic Building Blocks;Pyrrolidines
• Mol File: 62617-70-3.mol
• Article Data: 14

Chemical Properties

• Flash Point: 7 °C
• Appearance: /
• Density: 0.852 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.431
• Storage Temp.: 2-8°C
• BRN: 4652641
• CAS DataBase Reference: (2R,5R)-(-)-TRANS-2,5-DIMETHYLPYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5R)-(-)-TRANS-2,5-DIMETHYLPYRROLIDINE(62617-70-3)
• EPA Substance Registry System: (2R,5R)-(-)-TRANS-2,5-DIMETHYLPYRROLIDINE(62617-70-3)

Safety Data

• Hazard Codes: F,C
• Statements: 11-22-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2924 3/PG 2
• WGK Germany: 3
• F: 10-34
• Hazardous Substances Data: 62617-70-3(Hazardous Substances Data)

Usage

General Description

(2R,5R)-(-)-TRANS-2,5-DIMETHYLPYRROLIDINE is a chemical compound with a molecular formula of C7H13N. It is a chiral molecule that exists in two enantiomeric forms, with (2R,5R)-(-)-TRANS-2,5-DIMETHYLPYRROLIDINE being the optically active enantiomer. (2R,5R)-(-)-TRANS-2,5-DIMETHYLPYRROLIDINE is a cyclic secondary amine with a pyrrolidine ring structure and two methyl groups attached to the second and fifth carbon atoms of the ring. It is commonly used as a chiral auxiliary in organic synthesis and as a building block in the production of pharmaceuticals and other fine chemicals. Its specific stereochemistry and reactivity make it a valuable tool in asymmetric synthesis and other chemical transformations.

Upstream product

• 10345-32-1 (+/-)-trans-2,5-dimethyl-2,5-dihydro-pyrrole 
• 62564-43-6 (+/-)-2r,5t-dimethyl-pyrrolidinoamine 
• 7380-76-9 2-aminohex-5-ene 
• 625-84-3 2,5-Dimethylpyrrole 
• 55556-86-0 (+/-)-2r,5t-dimethyl-1-nitroso-pyrrolidine 

Downstream Products

• 55556-86-0 (+/-)-2r,5t-dimethyl-1-nitroso-pyrrolidine 
• 31163-31-2 (+/-)-2r,5t-dimethyl-pyrrolidine-1-carboxylic acid anilide 
• 878021-32-0 C₁₉H₃₂NO₂Si 
• 878021-25-1 2-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2,5-dimethyl-3,4-dihydro-2H-pyrrole 1-oxide 
• 132126-97-7 (R)-2-Cyclohexyl-1,4-bis-((2R,5R)-2,5-dimethyl-pyrrolidin-1-yl)-butane-1,4-dione 
• 132126-97-7 (S)-2-Cyclohexyl-1,4-bis-((2R,5R)-2,5-dimethyl-pyrrolidin-1-yl)-butane-1,4-dione 
• 136634-13-4 (2R,3S)-1-((2R,5R)-2,5-Dimethyl-pyrrolidin-1-yl)-2-fluoro-3-methyl-pentan-1-one 
• 136734-69-5 (2S,3S)-1-((2R,5R)-2,5-Dimethyl-pyrrolidin-1-yl)-2-fluoro-3-methyl-pentan-1-one 
• 168253-01-8 (2R,5R)-2,5-dimethylpyrrolidine-1-carbonyl chloride 
• 246236-69-1 (E)-1-((2R,5R)-2,5-Dimethyl-pyrrolidin-1-yl)-3-phenyl-propenone 
• 372514-02-8 [4'-(3-Chloro-propoxy)-biphenyl-4-yl]-((2R,5R)-2,5-dimethyl-pyrrolidin-1-yl)-methanone 

Relevant articles and documents

Reactivity of functionalized indoles with rare-earth metal amides. Synthesis, characterization and catalytic activity of rare-earth metal complexes incorporating indolyl ligands

The reactivity of several functionalized indoles 2-(RNHCH2)C8H5NH (R = C6H5 (1), tBu (2), 2,6-iPr2C6H3 (3)) with rare-earth metal amides is described. Reactions of 1 or 2 with [(Me3Si)2N]3RE(μ-Cl)Li(THF)3 (RE = Eu, Yb) respectively produced the europium complexes [2-(C6H5NCH)C8H5N]2Eu[N(SiMe3)2] (4) and [2-(tBuNCH)C8H5N]Eu[N(SiMe3)2]2 (5), and the ytterbium complex [2-(tBuNCH)C8H5N]2Yb[N(SiMe3)2] (6), containing bidentate anionic indolyl ligands via dehydrogenation of the amine to the imine. In contrast, reactions of the more sterically bulky indole 3 with [(Me3Si)2N]3RE(μ-Cl)Li(THF)3 afforded complexes [2-(2,6-iPr2C6H3NCH2)C8H5N]RE[N(SiMe3)2](THF)2 (RE = Yb (7), Y (8), Er (9), Dy (10)) with the deprotonated indolyl ligand. While reactions of 3 with yttrium and ytterbium amides in refluxing toluene respectively gave the complexes [2-(2,6-iPr2C6H3NCH)C8H5N]3Y (11) and [2-(2,6-iPr2C6H3NCH)C8H5N]2YbII(THF)2 (12), along with transformation of the amino group to the imino group, and also with a reduction of Yb3+ to Yb2+ in the formation of 12. Reactions of 3 with samarium and neodymium amides provided novel dinuclear complexes {[μ-η5:η1:η1-2-(2,6-iPr2C6H3NCH2)C8H5N]RE[N(SiMe3)2]}2 (RE = Sm (13), Nd (14)) having indolyl ligands in μ-η5:η1:η1 hapticities. The pathway for the transformation of the amino group to the imino group is proposed on the basis of the experimental results. The new complexes displayed excellent activity in the intramolecular hydroamination of aminoalkenes.

Highly active and diastereoselective N,O- and N,N-yttrium complexes for intramolecular hydroamination

The intramolecular hydroamination of aminoalkynes and unactivated aminoalkenes catalyzed by yttrium N,O- and N,N-complexes has been investigated. The N,N-yttrium complexes are highly active, catalyzing the conversion of a wide range of terminal aminoalkenes at room temperature, and internal aminoalkenes at elevated temperature, to yield pyrrolidine and piperidine products in high yields. A high diastereoselectivity of up to 23:1 is observed at 0°C with 1-methyl-4-pentenylamine as substrate.

C2-symmetric zirconium Bis(Amidate) complexes with enhanced reactivity in aminoalkene hydroamination

Binaphthalenedicarboxamide zirconium complexes exhibit significantly enhanced catalytic activity in aminoalkene hydroamination reactions with respect to substrate scope (substrates without gem-dialkyl activation; cyclization of aminoheptenes), catalyst loading (as low as 0.5 mol %) and reaction temperatures (as low as 70 °C) compared to previous group 4 metal-based hydroamination catalyst systems.