109960-55-6

Basic information

• Product Name: ((S)-1-((R)-1-phenylethyl)pyrrolidin-3-yl)methanol
• Synonyms: ((S)-1-((R)-1-phenylethyl)pyrrolidin-3-yl)methanol;(S)-1-[(R)-1-Phenylethyl]-3-(hydroxyMethyl)pyrrolidine
• CAS NO: 109960-55-6
• Molecular Formula: C₁₃H₁₉NO
• Molecular Weight: 205
• Mol File: 109960-55-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ((S)-1-((R)-1-phenylethyl)pyrrolidin-3-yl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: ((S)-1-((R)-1-phenylethyl)pyrrolidin-3-yl)methanol(109960-55-6)
• EPA Substance Registry System: ((S)-1-((R)-1-phenylethyl)pyrrolidin-3-yl)methanol(109960-55-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 109960-55-6(Hazardous Substances Data)

Usage

General Description

((S)-1-((R)-1-phenylethyl)pyrrolidin-3-yl)methanol is a chemical compound that belongs to the group of alkaloids and derivatives. It plays a significant role in various research fields owing to its stereochemical structure. The structure of this compound comprises a pyrrolidine ring, which is a type of cyclic amine, connected to a phenylethyl moiety and a methanol group. Particularly, the compound possesses a chiral center that gives it the character of stereoisomerism. This chemical is not overly prevalent in commercial uses or widespread consumer products, but it is related to stereoisomerism and enantioselectivity studies, and it could be used as a precursor for the synthesis of pharmaceutical compounds.

Upstream product

• 99735-46-3 methyl (3S)-1-<(R)-1-phenylethyl>-5-oxo-3-pyrrolidinecarboxylate 
• 215183-32-7 (4S,1'R)-1-(1'-phenylethyl)-4-hydroxymethylpyrrolidin-2-one 
• 252051-19-7 (4S,1'R)-[1-(1'-phenylethyl)-2-oxopyrrolidin-4-yl]carboxaldehyde 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 915302-94-2 (3RS)-1-<(R)-1-phenylethyl>-5-oxo-3-pyrrolidinecarboxylic acid 
• 617-52-7 Dimethyl itakonate 
• 97-65-4 2-methylenesuccinic acid 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 

Downstream Products

• 109960-56-7 (3S)-1-<(R)-1-phenylethyl>-3-(chloromethyl)pyrrolidine 
• 110013-19-9 (S)-(-)-3-(hydroxymethyl)pyrrolidine 
• 199174-24-8 tert-butyl (3S)-3-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 252051-25-5 (3S,1'R)-1-(1'-phenylethyl)-3-methanesulfonyloxymethylpyrrolidine 
• 882868-71-5 Benzyl-(S)-1-pyrrolidin-3-ylmethyl-amine 
• 109960-57-8 Ethyl-[(R)-1-((R)-1-phenyl-ethyl)-pyrrolidin-3-ylmethyl]-amine 
• 1264942-79-1 (3S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1-[(1R)-1-phenylethyl]pyrrolidine 
• 122408-84-8 (3R)-1-<(R)-1-phenylethyl>-3-(cyanomethyl)pyrrolidine 
• 122442-01-7 (R)-(-)-3-pyrrolidineacetic acid 
• 122408-85-9 (3R)-methyl 1-<(R)-1-phenylethyl>pyrrolidine-3-acetate hydrochloride 

Relevant articles and documents

Synthesis and determination of absolute configuration of a non-peptidic αvβ6 integrin antagonist for the treatment of idiopathic pulmonary fibrosis

A diastereoselective synthesis of (S)-3-(3-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl)-4-((R)-3-(2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)butanoic acid (1), a potential therapeutic agent for the treatment of Idiopathic Pulmonary Fibrosis, which is currently undergoing Phase I clinical trials is reported. The key steps in the synthesis involved alkylation of 2-methylnaphthyridine with (R)-N-Boc-3-(iodomethyl)-pyrrolidine, and an asymmetric Rh-catalysed addition of an arylboronic acid to a 4-(N-pyrrolidinyl)crotonate ester. The overall yield of the seven linear step synthesis was 8% and the product was obtained in >99.5% ee proceeding with 80% de. The absolute configuration of 1 was established by an alternative asymmetric synthesis involving alkylation of an arylacetic acid using Evans oxazolidinone chemistry, acylation using the resulting 2-arylsuccinic acid, and reduction. The absolute configuration of the benzylic asymmetric centre was established as (S).

4-Piperidines and 3-pyrrolidines as dual serotonin and noradrenaline reuptake inhibitors: Design, synthesis and structure-activity relationships

Single enantiomer [(aryloxy)(pyridinyl)methyl]piperidine and pyrrolidine derivatives 5-9 are inhibitors of monoamine reuptake. Structure-activity relationships established that monoamine reuptake inhibition are functions of amine, pyridine isomer, aryloxy ring substitution and stereochemistry. Consequently, selective NRIs, selective SRIs, dual SNRIs and triple SNDRIs were all identified. Dual SNRIs 5l-a and 9c were evaluated in additional pharmacology and pharmacokinetic studies as representative examples from this series.

GABA Agonists and Uptake Inhibitors. Synthesis, Absolute Stereochemistry, and Enantioselectivity of (R)-(-)- and (S)-(+)-Homo-β-proline

The cyclic analogue of 4-aminobutyric acid (GABA), 3-pyrrolidineacetic acid (homo-β-proline), is a potent agonist at GABAA receptors, it interacts effectively with GABA-uptake mechanisms, and it is a moderately potent inhibitor of GABAB/s