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.

Dihydrogen-Driven NADPH Recycling in Imine Reduction and P450-Catalyzed Oxidations Mediated by an Engineered O2-Tolerant Hydrogenase

The O2-tolerant NAD+-reducing hydrogenase (SH) from Ralstonia eutropha (Cupriavidus necator) has already been applied in vitro and in vivo for H2-driven NADH recycling in coupled enzymatic reactions with various NADH-dependent oxidoreductases. To expand the scope for application in NADPH-dependent biocatalysis, we introduced changes in the NAD+-binding pocket of the enzyme by rational mutagenesis, and generated a variant with significantly higher affinity for NADP+ than for the natural substrate NAD+, while retaining native O2-tolerance. The applicability of the SH variant in H2-driven NADPH supply was demonstrated by the full conversion of 2-methyl-1-pyrroline into a single enantiomer of 2-methylpyrrolidine catalysed by a stereoselective imine reductase. In an even more challenging reaction, the SH supported a cytochrome P450 monooxygenase for the oxidation of octane under safe H2/O2 mixtures. Thus, the re-designed SH represents a versatile platform for atom-efficient, H2-driven cofactor recycling in biotransformations involving NADPH-dependent oxidoreductases.

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.