104641-59-0

Basic information

• Product Name: (S)-(+)-1-Methyl-3-pyrrolidinol
• Synonyms: (S)-3-HYDROXY-1-METHYL-PYRROLIDINE;(R)-3-Hydroxy-1-methylpyr...;(S)-(+)-1-Methyl-3-pyrrolidinol, ee 99%, 98%;(S)-(+)-1-Methyl-3-pyrrolidinol, 98%, ee 99%;(3S)-1-methylpyrrolidin-3-ol;(S)-(+)-1-Methyl-3-pyrrolidinol 95%;(S)-N-Methyl-3-pyrrolidinol;(S)-N-Methyl-3-pyrrolidinol,99%e.e.
• CAS NO: 104641-59-0
• Molecular Formula: C₅H₁₁NO
• Molecular Weight: 101.15
• EINECS: -0
• Product Categories: Pyrrole&Pyrrolidine&Pyrroline;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry
• Mol File: 104641-59-0.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 181-182 °C(lit.)
• Flash Point: 192 °F
• Appearance: Colorless to yellow to brown/Liquid
• Density: 0.993 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.132mmHg at 25°C
• Refractive Index: n20/D 1.4660(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 14.95±0.20(Predicted)
• Sensitive: Air Sensitive & Hygroscopic
• BRN: 4349394
• CAS DataBase Reference: (S)-(+)-1-Methyl-3-pyrrolidinol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-1-Methyl-3-pyrrolidinol(104641-59-0)
• EPA Substance Registry System: (S)-(+)-1-Methyl-3-pyrrolidinol(104641-59-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• RTECS: TM9570000
• Hazardous Substances Data: 104641-59-0(Hazardous Substances Data)

Usage

Description

(S)-(+)-1-Methyl-3-pyrrolidinol is a chiral organic compound that serves as a valuable synthetic intermediate in the pharmaceutical industry. It is characterized by its unique stereochemistry and versatile functional groups, which enable its use in the synthesis of various biologically active molecules.

Uses

Used in Pharmaceutical Industry:
(S)-(+)-1-Methyl-3-pyrrolidinol is used as a synthetic intermediate for the preparation of diaryl acylaminopyrimidines, which act as adenosine A2A antagonists. These antagonists have potential applications in the treatment of various neurological disorders, such as Parkinson's disease, by modulating the adenosine signaling pathway.
Additionally, (S)-(+)-1-Methyl-3-pyrrolidinol is utilized in the synthesis of (alkoxyamino)(pyridinylamino)pyrazinecarbonitriles, which are selective checkpoint kinase 1 (CHK1) inhibitors. These inhibitors exhibit oral antitumor activities and have potential applications in cancer therapy, particularly for the treatment of solid tumors. By targeting the CHK1 enzyme, these inhibitors can disrupt the cell cycle and induce apoptosis in cancer cells, offering a promising approach for cancer treatment.

InChI:InChI=1/C5H11NO/c1-6-3-2-5(7)4-6/h5,7H,2-4H2,1H3/t5-/m0/s1

Upstream product

• 68165-06-0 1-methylpyrrolidin-3-one 
• 50-00-0 formaldehyd 
• 122536-94-1 (S)-3-hydroxypyrrolidine hydrochloride 
• 1104643-24-4 (S)-3-tert-butoxy-N-methylpyrrolidine 
• 104612-35-3 (S)-3-hydroxy-1-methyl-2,5-pyrrolidinedione 

Downstream Products

• 207856-83-5 3'(S)-N-methyl-3'-pyrrolidinyl (R)-cyclopentylmandelate 
• 207856-85-7 (3S)-1-methylpyrrolidin-3-yl (2R)-2-cyclopentyl-2-hydroxy-2-phenylacetate 
• 1610372-32-1 (S)-7-fluoro-5-((1-methylpyrrolidin-3-yl)oxy)-2-(6-(4-(methylsulfonyl)phenyl)pyridin-2-yl)quinazolin-4(3H)-one 
• 1219727-20-4 (S)-1-ethyl-1-(3-methoxybenzyl)-3-(2-(1-methylpyrrolidin-3-yloxy)-4-(1H-pyrazol-4-yl)phenyl)urea 
• 1219731-41-5 C₂₂H₂₈BrN₃O₃ 
• 1428555-12-7 C₂₀H₂₂BrF₃N₂O₅S 
• 1428555-20-7 C₁₂H₁₃F₃N₂O₃ 
• 1231955-04-6 N-[(2Z)-5-tert-butyl-3-isobutyl-1,3-thiazol-2(3H)-ylidene]-2-{[(3S)-1-methylpyrrolidin-3-yl]oxy}-5-(trifluoromethyl)benzamide 
• 1159928-86-5 [(3S)-1-methylpyrrolidin-3-yl]-4-(4-methylphenyl)piperazine-1-carboxylate 
• 1061749-62-9 N-{2-(3,5-dimethyl-pyrazol-1-yl)-6-[3-((S)-1-methyl-pyrrolidin-3-yloxymethyl)-phenyl]-pyrimidin-4-yl}-acetamide 
• 1061749-27-6 C₂₂H₂₆N₆O₂ 
• 1061748-77-3 C₂₂H₂₅FN₆O₂ 
• 1140918-80-4 (S)-2-(1-methylpyrrolidin-3-yloxy)-5-(trifluoromethyl)benzonitrile 
• 1033594-21-6 3-[4-((3R)-hydroxymethyl-3,4-dihydro-1H-isoquinolin-2-yl)-6-(1-methyl-pyrrolidin-3(S)-yloxy)-[1,3,5]triazin-2-yl]-phenol 

Relevant articles and documents

Widely applicable background depletion step enables transaminase evolution through solid-phase screening

Directed evolution of transaminases is a widespread technique in the development of highly sought-after biocatalysts for industrial applications. This process, however, is challenged by the limited availability of effective high-throughput protocols to evaluate mutant libraries. Here we report a rapid, reliable, and widely applicable background depletion method for solid-phase screening of transaminase variants, which was successfully applied to a transaminase from Halomonas elongata (HEWT), evolved through rounds of random mutagenesis towards a series of diverse prochiral ketones. This approach enabled the identification of transaminase variants in viable cells with significantly improved activity towards para-substituted acetophenones (up to 60-fold), as well as tetrahydrothiophen-3-one and related substrates. Rationalisation of the mutants was assisted by determination of the high-resolution wild-type HEWT crystal structure presented herein.

PROCESS FOR THE EFFICIENT PREPARATION OF 3-HYDROXY PYRROLIDINE AND DERIVATIVES THEREOF

The present invention relates to an effective process for the preparation of 3-hydroxypyrrolidine or derivatives thereof. The process comprises (a) protecting a hydroxyl group of 4-halo-3-hydroxybutyric acid, (b) reducing an ester group of the compound obtained from the step (a) to obtain a corresponding alcohol compound, (c) reacting the compound obtained from the step (b) with sulfonyl halide to produce a corresponding sulfonate compound, (d) reacting the compound obtained from the step (c) with an amine to obtain 3-hydroxy-protected pyrrolidine compound, and (e) deprotecting the compound obtained from the step (d) to produce the targeted 3-hydroxypyrrolidine or derivatives thereof. The process provides 3-hydroxypyrrolidine or derivatives thereof with high optical purity, because optical purity of the starting material is substantially retained. In the process, each of the steps is carried out in a mild condition and does not require any special purification. This means that the process is useful and adequate for industrial mass production of 3-hydroxypyrrolidine and derivatives thereof having high optical purity.

SOFT ANTICHOLINERGIC ESTERS

Soft anticholinergic esters of the formulas: wherein R1 and R2 are both phenyl or one of R1 and R2 is phenyl and the other is cyclopentyl; R is C1-C8 alkyl, straight or branched chain; and X- is an anion with a single negative charge; and wherein each asterisk marks a chiral center; said compound having the R, S or RS stereoisomeric configuration at each chiral center unless specified otherwise, or being a mixture thereof.