117968-50-0

Basic information

• Product Name: (2S,5S)-2,5-Dimethyl-pyrrolidine
• CAS NO: 117968-50-0
• Molecular Weight: 0
• Mol File: 117968-50-0.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: (2S,5S)-2,5-Dimethyl-pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5S)-2,5-Dimethyl-pyrrolidine(117968-50-0)
• EPA Substance Registry System: (2S,5S)-2,5-Dimethyl-pyrrolidine(117968-50-0)

Safety Data

• Hazardous Substances Data: 117968-50-0(Hazardous Substances Data)

Usage

General Description

(2S,5S)-2,5-Dimethyl-pyrrolidine is a chemical compound with a molecular formula of C7H13N. It is a derivative of pyrrolidine, a five-membered heterocyclic organic compound. The specific stereochemistry of (2S,5S) refers to its chirality or three-dimensional arrangement of atoms, which can have implications for its biological activity and reactivity. (2S,5S)-2,5-Dimethyl-pyrrolidine has various industrial applications, including as a chiral building block for the synthesis of pharmaceuticals and agrochemicals. It is also used as a solvent and a reagent in organic synthesis. Overall, (2S,5S)-2,5-Dimethyl-pyrrolidine is a versatile compound with important applications in both the chemical and pharmaceutical industries.

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 
• 55556-86-0 (+/-)-2r,5t-dimethyl-1-nitroso-pyrrolidine 
• 625-84-3 2,5-Dimethylpyrrole 

Downstream Products

• 129539-96-4 (2S-trans)-2,5-Dimethyl-1-<1-oxo-5-(phenylmethoxy)-pentyl>pyrrolidine 
• 136734-70-8 (2R,3S)-1-((2S,5S)-2,5-Dimethyl-pyrrolidin-1-yl)-2-fluoro-3-methyl-pentan-1-one 
• 136734-71-9 (2S,3S)-1-((2S,5S)-2,5-Dimethyl-pyrrolidin-1-yl)-2-fluoro-3-methyl-pentan-1-one 
• 1053637-11-8 (4S,5R,6R)-5-Acetylamino-4-tert-butoxycarbonylamino-6-((2S,5S)-2,5-dimethyl-pyrrolidine-1-carbonyl)-5,6-dihydro-4H-pyran-2-carboxylic acid benzhydryl ester 
• 618386-92-8 (2S,5S)-1-[(4R)-4-nemzoyloxy-5-vinylhept-6-enoyl]-2,5-dimethylpyrrolidine 
• 139135-92-5 (2S,5S)-1-[(4R)-4-(tert-butyldiphenylsilyloxy)-5-vinylhept-6-enoyl]-2,5-dimethylpyrrolidine 
• 139108-42-2 (2S,5S)-1-[(4S)-4-(tert-butyldiphenylsilyloxy)-5-vinylhept-6-enoyl]-2,5-dimethylpyrrolidine 
• 1599447-18-3 1-[(2S,5S)-2,5-dimethylpyrrolidin-1-yl]-2-(2-hydroxyphenyl)ethanone 
• 129539-97-5 Methyl <2S-<1*<1R^*,1(E),2S^*>>,2α,5β>>-1-(4,8-Dimethyl-3,7-nonadienyl)-2-<1-<(2,5-dimethyl-1-pyrrolidinyl)carbonyl>-4-(phenylmethoxy)butyl>cyclopentanecarboxylate 
• 129539-98-6 <2S-<1*<1R^*,2S^*,2(E)>>,2α,5β>>-1-<2-<2-(4,8-Dimethyl-3,7-nonadienyl)-2-(hydroxymethyl)cyclopentyl>-1-oxo-5-(phenylmethoxy)pentyl>-2,5-dimethylpyrrolidine 
• 117982-39-5 (S)-5-Benzyl-4-((2S,5S)-2,5-dimethyl-pyrrolidin-1-yl)-3-methyl-5H-furan-2-one 
• 117982-39-5 (R)-5-Benzyl-4-((2S,5S)-2,5-dimethyl-pyrrolidin-1-yl)-3-methyl-5H-furan-2-one 
• 117968-61-3 (S)-5-Benzyl-4-((2S,5S)-2,5-dimethyl-pyrrolidin-1-yl)-5H-furan-2-one 
• 117968-61-3 (R)-5-Benzyl-4-((2S,5S)-2,5-dimethyl-pyrrolidin-1-yl)-5H-furan-2-one 

Relevant articles and documents

Internal alkene hydroaminations catalyzed by zirconium(IV) complexes and asymmetric alkene hydroaminations catalyzed by yttrium(III) complexes

The thiophosphinic amide 2 was prepared in 68% yield by the reaction of 2,2-dimethyl-1,3-propanediamine with diisopropylchlorophosphine followed by the addition of sulfur. Attachment of the proligand 2 to zirconium was achieved by direct metalation with Zr(NMe2)4 in benzene-d6 or toluene-d8 to afford complex 3 via elimination of dimethylamine. The neutral Zr(IV) complex 3 has been shown to be an effective precatalyst for intramolecular alkene hydroaminations that provide cyclic amines in good to excellent yields. A variety of chiral ligands (20, 22, 24, and 25-30) were prepared for asymmetric internal alkene hydroaminations. Metalation of chiral ligands to yttrium was accomplished with Y[N-(TMS)2]3 in benzene-d6 or toluene-d8 to give complexes. Treatment of 7 with 5 mol% of 33 in benzene-d6 (25°C, 18 h) or toluene-d 8 (25°C, 15 h) afforded 2,4,4-trimethylpyrrolidine 14 in 95% yield (61% ee).

Intramolecular alkene hydroaminations catalyzed by simple amido derivatives of the Group 3 metals

Bis(trimethylsilyl) amides of the type Ln[N(TMS) 2]3 have been found to be competent catalysts for representative intramolecular alkene hydroaminations. The catalytic cyclization of an aminodiene proceeds in a stepwise manner to provide the corresponding monocycle and bicycle in a highly stereocontrolled manner.

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.