54677-53-1

Basic information

• Product Name: 2-METHYLPYRROLIDINE HYDROCHLORIDE
• Synonyms: 2-METHYLPYRROLIDINE HYDROCHLORIDE;Pyrrolidine, 2-Methyl-, hydrochloride
• CAS NO: 54677-53-1
• Molecular Formula: C₅H₁₁N*ClH
• Molecular Weight: 121.61
• Mol File: 54677-53-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• Water Solubility: Soluble in water
• CAS DataBase Reference: 2-METHYLPYRROLIDINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYLPYRROLIDINE HYDROCHLORIDE(54677-53-1)
• EPA Substance Registry System: 2-METHYLPYRROLIDINE HYDROCHLORIDE(54677-53-1)

Safety Data

• Statements: 36/38
• Safety Statements: 26-36
• Hazardous Substances Data: 54677-53-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
2-Methylpyrrolidine hydrochloride is used as a building block for the creation of various pharmaceuticals and agrochemicals, leveraging its chemical properties to facilitate the development of new compounds.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
In the field of asymmetric synthesis, 2-Methylpyrrolidine hydrochloride is utilized as a chiral auxiliary, playing a crucial role in the selective formation of enantiomers, which is vital for the production of biologically active molecules.
Used as a Reaction Solvent:
2-Methylpyrrolidine hydrochloride serves as a solvent for a range of chemical reactions, providing a medium that supports the process and improves the yield of desired products.
Used in Nicotine Addiction Treatment:
2-Methylpyrrolidine hydrochloride is explored as a potential treatment for nicotine addiction, acting as a partial agonist for nicotinic acetylcholine receptors, which may help in managing nicotine cravings and aiding in smoking cessation therapies.
Proper handling and storage are essential to maintain the safety and effectiveness of 2-Methylpyrrolidine hydrochloride for its intended applications across different industries.

Upstream product

• 338945-22-5 (S)-2-iodomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 43041-12-9 methyl (2R)-pyrrolidine-2-carboxylate 
• 124-63-0 methanesulfonyl chloride 
• 132482-09-8 tert-butyl (2S)-2-{[(methylsulfonyl)oxy]methyl}-pyrrolidine-1-carboxylate 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 157007-54-0 2-(R)-methylpyrrolidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 636-41-9 2-methyl-1H-pyrrole 
• 460747-73-3 (R)-1-(but-3-yn-1-yl)-2-methylpyrrolidine 
• 1005402-80-1 4-{4-[3-((R)-2-methyl-pyrrolidin-1-yl)-propoxy]-phenyl}-4-oxo-butyric acid ethyl ester 
• 1005402-84-5 3,3-dimethyl-4-{4-[3-((R)-2-methyl-pyrrolidin-1-yl)-propoxy]-phenyl}-4-oxo-butyric acid ethyl ester 
• 876617-01-5 2-[2-(4-benzyloxy-phenyl)-5-methyl-oxazol-4-yl]-1-(2-(R)-methyl-pyrrolidin-1-yl)-ethanone 
• 876617-65-1 2-(4-bromophenyl)-4-{2-[(2R)-2-methylpyrrolidin-1-yl]ethyl}-5-methyl-1,3-oxazole 
• 876617-04-8 2-{2-[6-(4-methanesulfonyl-phenyl)-pyridin-3-yl]-5-methyl-oxazol-4-yl}-1-(2-(R)-methyl-pyrrolidin-1-yl)-ethanone 
• 921616-75-3 1,1-dimethylethyl 4-[4-({3-[(R)-2-methyl-1-pyrrolidinyl]propyl}oxy)phenyl]-3-oxo-1-piperazinecarboxylate 
• 1018966-12-5 3-[(4-{2-[(2R)-2-methylpyrrolidin-1-yl]ethoxy}phenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]pyridine-2-carboxamide 
• 1005403-35-9 (R)-2-methyl-1-{3-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenoxyl]propyl}pyrrolidine 
• 1260098-21-2 2-methyl-1-{4-[3-((R)-2-methyl-pyrrolidin-1-yl)-propoxy]-phenyl}-2-morpholin-4-yl-propan-1-one 

Relevant articles and documents

Production method of (R)-2-methylpyrrolidine hydrochloride

The invention provides a production method of (R)-2-methylpyrrolidine hydrochloride. The method is an industrial production method and adopts a reduction method of sodium borohydride and different solvents to obtain the (R)-2-methylpyrrolidine hydrochloride with the product purity of 98% or above and the product total yield of 70% or above. Also provided is a process for the synthesis of chiral (R)-2-methylpyrrolidine hydrochloride. Meanwhile, raw materials adopted in the method are easy to obtain, synthesis conditions are simple, the product yield is high, and the method is suitable for industrial production.

Asymmetric synthesis of chiral cyclic amine from cyclic imine by bacterial whole-cell catalyst of enantioselective imine reductase

Streptomyces sp. GF3587 and 3546 were found to be imine-reducing strains with high R- and S-selectivity by screening using 2-methyl-1-pyrroline (2-MPN). Their whole-cell catalysts produced 91 mM R-2-methylpyrrolidine (R-2-MP) with 99.2%e.e. and 27.5 mM S-2-MP (92.3%e.e.) from 2-MPN at 91-92% conversion in the presence of glucose, respectively.

MODULATORS OF THE HISTAMINE H3-RECEPTOR USEFUL FOR THE TREATMENT OF DISORDERS RELATED THERETO

The present invention relates to certain biphenyl sulfonamide derivatives of Formula (Ia) and pharmaceutical compositions thereof that modulate the activity of the histamine H3-receptor. Compounds and pharmaceutical compositions thereof are directed to methods useful in the treatment of histamine H3-receptor associated disorders, such as, cognitive disorders, epilepsy, brain trauma, depression, obesity, disorders of sleep and wakefulness such as narcolepsy, hypersomnia, somnolence syndrome, jet lag, sleep apnea and the like, attention deficit hyperactivity disorder (ADHD), schizophrenia, allergies, allergic responses in the upper airway, allergic rhinitis, nasal congestion, dementia, Alzheimer's disease and the like.

An efficient and convergent synthesis of the potent and selective H3 antagonist ABT-239

An efficient and convergent process for the preparation of a potent and selective H3 receptor antagonist, ABT-239, 1A was accomplished with an overall yield of 64%. The key step in the synthesis is a Sonogashira coupling/cyclization reaction of 1-but-3-ynyl-2-(R)-methylpyrrolidine (9) with 4′-hydroxy-3′-iodo-biphenyl-4-carbonitrile (3). Additionally, the key amine component 2-(R)-methylpyrrolidine (7) was effectively synthesized from the readily available Boc-l-prolinol with a simple catalytical hydrogenolysis as the key step. This column chromatography-free process is highlighted by several simple work-up and purification procedures and is amendable to the large-scale preparation of 1A.

OXAZOLE DERIVATIVES AS HISTAMINE H3 RECEPTOR AGENTS, PREPARATION AND THERAPEUTIC USES

The present invention discloses novel aryl oxazole compounds of Formula I (I), or pharmaceutically acceptable salts thereof, which have histamine-H3 receptor antagonist or inverse agonist activity, as well as methods for preparing and using such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising compounds of Formula I as well as methods of using these compositions to treat obesity, cognitive deficiencies, narcolepsy, and other histamine H3 receptor-related diseases. Formula I (I) or a pharmaceutically acceptable salt thereof, wherein: m is independenlly at each occurrence 1, 2, or 3, Z independently represents carbon (substituted with hydrogen or the optional substituents indicated herein) or nitrogen, provided that when Z is nitrogen then R6 is not attached to Z; R1 and R2 are independently -(C1-C7) alkyl(optionally substituted with one to three halogens), or R1 and R2 and the nitrogen to which they are attached form an azetidinyl ring, a pyrrolidinyl ring, or a piperidinyl ring, wherein further the azetidinyl, pyrrolidinyl, or piperidinyl ring so formed may be optionally substituted one to three times with R5; R6 is independently at each occurrence -H, -halogen, or -CH3.

Process for preparing 2-methylpyrrolidine and specific enantiomers thereof

The invention relates to a process for preparing 2-methylpyrrolidine and, more particularly, specific enantiomers of 2-methylpyrrolidine. Novel intermediates also are described.

Peptide derivatives having thiazolyl-alanine residue

A peptide derivation of the formula (I) or its pharmaceutically acceptable salt or hydrate thereof is disclosed. These compounds have superior ability over thyroid stimulating hormone (TRH) and its derivatives to activate the central nervous system, such as, for example, sustained acetylcholine releasing action, anti-reserpine action and locomotor increment.