59335-84-1

Basic information

• Product Name: (S)-2-Methyl-pyrrolidine
• Synonyms: (S)-(+)-2-METHYLPYRROLIDINE;(S)-2-METHYL-PYRROLIDINE;D-2-METHYLPYRROLIDINE;METHYLPYRROLIDINE(S-2-);(2S)-2-Methylpyrrolidine;2-(S)-METHYLPYRROLIDINE;(S)-(+)-2-Methylpyrrolidine 97%
• CAS NO: 59335-84-1
• Molecular Formula: C₅H₁₁N
• Molecular Weight: 85.15
• EINECS: 212-144-3
• Product Categories: Heterocyclic Series;Benzenes;Chiral Compound;Chiral Building Blocks;Heterocyclic Building Blocks;Pyrrolidines
• Mol File: 59335-84-1.mol
• Article Data: 41

Chemical Properties

• Boiling Point: 97-99 °C(lit.)
• Flash Point: 45 °F
• Appearance: /
• Density: 0.842 g/mL at 25 °C(lit.)
• Vapor Pressure: 37.1mmHg at 25°C
• Refractive Index: n20/D 1.4354
• Storage Temp.: 2-8°C
• PKA: 10.93±0.10(Predicted)
• CAS DataBase Reference: (S)-2-Methyl-pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-Methyl-pyrrolidine(59335-84-1)
• EPA Substance Registry System: (S)-2-Methyl-pyrrolidine(59335-84-1)

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: 2
• PackingGroup: Ⅱ
• Hazardous Substances Data: 59335-84-1(Hazardous Substances Data)

Usage

General Description

(S)-2-Methyl-pyrrolidine is a chemical compound that belongs to the class of heterocyclic compounds, specifically, pyrrolidines. It is a colorless liquid with a slightly ammonia-like odor and is commonly used as a building block in the synthesis of pharmaceuticals and other fine chemicals. The (S)-2-Methyl-pyrrolidine molecule consists of a five-membered ring with four carbon atoms and one nitrogen atom, with a methyl group attached to the second carbon. (S)-2-Methyl-pyrrolidine is known for its potential as a chiral catalyst in organic reactions and as a solvent in chemical reactions. It has also been studied for its potential use in the development of new materials and biomolecules.

InChI:InChI=1/C5H11N/c1-5-3-2-4-6-5/h5-6H,2-4H2,1H3/t5-/m0/s1

Upstream product

• 765-38-8 2-methyl-1-pyrrolidine 
• 122970-63-2 2-Methylpyrroline 
• 108-27-0 5-methylpyrrolidin-2-one 
• 22537-07-1 4-pentenyl-1-amine 
• 283610-03-7 (2R)-2-[(2'R)-2'-methyl-N-pyrrolidinyl]-2-phenyl-1-ethanol 
• 592-51-8 4-Pentenenitrile 
• 117607-13-3 (R)-2-methylpyrrolidine hydrobromide 
• 1009105-76-3 1-(4-chlorobenzyl)-2-methylpyrrolidine 
• 1218989-50-4 (R)-1-((S)-2-methyl-propane-2-sulfinyl)-2-methyl-pyrrolidine 
• 51547-88-7 (2R)-1-tosyl-2-methylpyrrolidine 
• 872-32-2 2-methyl-1H-pyrroline 
• 157007-54-0 2-(R)-methylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 

Downstream Products

• 158059-30-4 2,6-Bis<((S)-2-methyl-1-pyrrolidinyl)methyl>bromobenzene 
• 137496-71-0 2-methylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 91539-40-1 (S)-N-benzoyl-2-methylpyrrolidine 
• 91539-43-4 (S)-N-(2-methylbenzoyl)-2-methylpyrrolidine 
• 91539-44-5 (S)-N-(2,4,6-trimethylbenzoyl)-2-methylpyrrolidine 
• 102536-11-8 ((R)-2-Methyl-pyrrolidin-1-yl)-phenyl-amine 
• 124096-31-7 (R)-2,2,2-trifluoro-1-<2-(2-methyl-1-pyrrolidinyl)phenyl>ethanone 
• 460747-73-3 (R)-1-(but-3-yn-1-yl)-2-methylpyrrolidine 
• 689290-83-3 4-(6-{2-[(2R)-2-methyl-1-pyrrolidinyl]ethyl}-2-naphthyl)benzonitrile 
• 849519-42-2 (R)-1-[2-(4-bromo-phenyl)-ethyl]-2-methyl-pyrrolidine 
• 1004763-61-4 2-(4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-5-(morpholin-4-ylsulfonyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine 

Relevant articles and documents

Acylative kinetic resolution of racemic methyl-substituted cyclic alkylamines with 2,5-dioxopyrrolidin-1-yl (: R)-2-phenoxypropanoate

The diastereoselective acylation of a number of racemic methyl-substituted cyclic alkylamines with active esters of 2-phenoxypropanoic acid was studied in detail. The ester of (R)-2-phenoxypropanoic acid and N-hydroxysuccinimide was found to be the most selective agent. The highest stereoselectivity was observed in the kinetic resolution of racemic 2-methylpiperidine in toluene at -40 °C (selectivity factor s = 73) with the predominant formation of (R,R)-amide (93.7% de). To explain the observed stereoselectivity, DFT modelling of the transition states in the reactions of the title acylating agent with 2-methylpiperidine and 2-methylpyrrolidine was performed. The calculated values were in good agreement with experimental data. It has been demonstrated that the acylation proceeds via a concerted mechanism, in which the addition of an amine occurs simultaneously with the elimination of the hydroxysuccinimide fragment. The high stereoselectivity of the (R,R)-amide formation is largely ensured by the lower steric hindrances in the transition states as compared to the formation of (R,S)-amide.

Stereoselective Biotransformations of Cyclic Imines in Recombinant Cells of Synechocystis sp. PCC 6803

Light-driven biotransformations in recombinant cyanobacteria allow to employ photosynthetic water-splitting for cofactor-regeneration and thus, to save the use of organic electron donors. The genes of three recombinant imine reductases (IREDs) were expressed in the cyanobacterium Synechocystis sp. PCC 6803 and eight cyclic imine substrates were screened in whole-cell biotransformations. While initial reactions showed low to moderate rates, optimization of the reaction conditions in combination with promoter engineering allowed to alleviate toxicity effects and achieve full conversion of prochiral imines with initial rates of up to 6.3 mM h?1. The high specific activity of up to 22 U gCDW ?1 demonstrates that recombinant cyanobacteria can provide large amounts of NADPH during whole cell reactions. The excellent optical purity of the products with up to >99 %ee underlines the usefulness of cyanobacteria for the stereoselective synthesis of amines.

Synthesis and evaluation of in vivo anti-hypothermic effect of all stereoisomers of the thyrotropin-releasing hormone mimetic: Rovatirelin Hydrate

We discovered the orally active thyrotropin-releasing hormone (TRH) mimetic: (4S,5S)-5-methyl-N-{(2S)-1-[(2R)-2-methylpyrrolidin-1-yl]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl}-2-oxo-1,3-oxazolidine-4-carboxamide 1 (rovatirelin). The central nervous system (CNS) effect of rovatirelin after intravenous (iv) administration is 100-fold higher than that of TRH. As 1 has four asymmetric carbons in its molecule, there are 16 stereoisomers. We synthesized and evaluated the anti-hypothermic effect of all stereoisomers of 1, which has the (4S),(5S),(2S),(2R) configuration from the N-terminus to the C-terminus, in order to clarify the structure?activity relationship (SAR) of stereoisomers. The (4R),(5R),(2R),(2S)-isomer 16 did not show any anti-hypothermic effect. Only the (4S),(5S),(2S),(2S)-isomer 10, which has the (2S)-2-methylpyrrolidine moiety at the C-terminus showed the anti-hypothermic effect similar to 1. Stereoisomers, which have the (5R) configuration of the oxazolidinone at the N-terminus and the (2R) configuration at the middle-part, showed a much lower anti-hypothermic effect than that of 1. On the other hand, stereoisomers, which have the (4R) configuration of the oxazolidinone at the N-terminus or the (2S) configuration of the C-terminus, have little influence on the anti-hypothermic effect.