37675-20-0

Basic information

• Product Name: 3(R)-PIPERIDINEMETHANOL
• Synonyms: 3(R)-PIPERIDINEMETHANOL;((R)-piperidin-3-yl)methanol;2,4-diiodo-6-fluoroaniline;(3R)-piperidin-3-ylMethanol;3-PiperidineMethanol,(3R)-;(R)-(+)-3-(Hydroxymethyl)piperidine;(3R)-3-Piperidinemethanol
• CAS NO: 37675-20-0
• Molecular Formula: C₆H₁₃NO
• Molecular Weight: 115.17352
• Mol File: 37675-20-0.mol

Chemical Properties

• Boiling Point: 240.4°C at 760 mmHg
• Flash Point: 92.3°C
• Appearance: /
• Density: 0.951g/cm³
• Vapor Pressure: 0.00664mmHg at 25°C
• Refractive Index: 1.451
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 14.93±0.10(Predicted)
• CAS DataBase Reference: 3(R)-PIPERIDINEMETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3(R)-PIPERIDINEMETHANOL(37675-20-0)
• EPA Substance Registry System: 3(R)-PIPERIDINEMETHANOL(37675-20-0)

Safety Data

• Hazardous Substances Data: 37675-20-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
3(R)-PIPERIDINEMETHANOL is used as a key intermediate in the synthesis of new drugs, leveraging its unique structure to create innovative pharmaceutical compounds with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 3(R)-PIPERIDINEMETHANOL is utilized as a building block for the creation of complex organic compounds, contributing to the advancement of chemical reactions and the development of novel chemical entities.
Used in Enantioselective Reactions:
3(R)-PIPERIDINEMETHANOL, being a specific enantiomer, is employed in enantioselective reactions to produce chiral compounds with desired stereochemistry, which is crucial for the efficacy and safety of pharmaceutical products.
Used in Drug Design:
3(R)-PIPERIDINEMETHANOL is used as a structural component in drug design, where its unique properties can be harnessed to develop drugs with improved pharmacokinetics, pharmacodynamics, and selectivity for specific biological targets.

InChI:InChI=1/C6H13NO/c8-5-6-2-1-3-7-4-6/h6-8H,1-5H2/t6-/m1/s1

Upstream product

• 37675-18-6 (S)-(+)-nipecotic acid ethyl ester 
• 71962-74-8 Ethyl nipecotate 
• 5621-43-2 diethyl 2-methyleneglutarate 
• 851956-01-9 (S)-(+)-3-piperidinecarboxylic acid hydrochloride 
• 140645-20-1 t-butyl (R,S)-3-<(butyryloxy)methyl>-1-piperidine-carboxylate 
• 175694-36-7 (3R,5S)-Piperidine-1,3,5-tricarboxylic acid 1-benzyl ester 3-methyl ester 
• 88466-73-3 Z-β²hPro-OMe 
• 1221818-73-0 (3S,5R)-Piperidine-1,3,5-tricarboxylic acid benzyl ester dimethyl ester 
• 405061-52-1 N-Cbz-3-hydroxymethylpiperidine 
• 140695-84-7 tert-butyl (3S)-3-(hydroxymethyl)piperidine-1-carboxylate 
• 498-95-3 (R)-nipecotic acid 

Downstream Products

• 191092-07-6 (R)-tert-butyl 3-((tosyloxy)methyl)piperidine-1-carboxylate 
• 116574-71-1 tert-butyl (3R)-3-(hydroxymethyl)piperidine-1-carboxylate 
• 155541-67-6 (R)-3-(azidomethyl)piperidine-1-carboxylic acid tert-butyl ester 
• 140645-24-5 tert-butyl (3S)-3-(aminomethyl)piperidine-1-carboxylate 

Relevant articles and documents

Manganese Catalyzed Hydrogenation of Enantiomerically Pure Esters

A manganese-catalyzed hydrogenation of esters has been accomplished with TONs up to 1000, using cheap, environmentally benign, potassium carbonate and simple alcohols as activator and solvent, respectively. The weakly basic conditions lead to good functional group tolerance and enable the hydrogenation of enantiomerically enriched α-chiral esters with essentially no loss of stereochemical integrity.

O-(α-Phenylethyl)hydroxylamine as a ‘chiral ammonia equivalent’: synthesis and resolution of 5-oxopyrrolidine- and 6-oxopiperidine-3-carboxylic acids

An approach to the synthesis and resolution of five- and six-membered lactams (i.e., 5-oxopyrrolidine- and 6-oxopiperidine-3-carboxylic acids) is described. The method relies on the one-pot Michael reaction—cyclization of itaconic acid or diethyl homoitaconate and enantiopure O-(α-phenylethyl)hydroxylamine as a ‘chiral ammonia equivalent’. It is shown that this chiral auxiliary can be used for the separation of diastereomeric lactam products and then easily removed by catalytic hydrogenolysis.

Design, synthesis, and biological evaluation of simplified side chain hybrids of the potent actin binding polyketides rhizopodin and bistramide

The natural products rhizopodin and bistramide belong to an elite class of highly potent actin binding agents. They show powerful antiproliferative activities against a range of tumor cell lines, with IC50 values in the low-nanomolar range. At the molecular level they disrupt the actin cytoskeleton by binding specifically to a few critical sites of G-actin, resulting in actin filament stabilization. The important biological properties of rhizopodin and bistramide, coupled with their unique and intriguing molecular architectures, render them attractive compounds for further development. However, this is severely hampered by the structural complexity of these metabolites. We initiated an interdisciplinary approach at the interface between molecular modeling, organic synthesis, and chemical biology to support further biological applications. We also wanted to expand structure-activity relationship studies with the goal of accessing simplified analogues with potent biological properties. We report computational analyses of actin-inhibitor interactions involving molecular docking, validated on known actin binding ligands, that show a close match between the crystal and modeled structures. Based on these results, the ligand shape was simplified, and more readily accessible rhizopodin-bistramide mimetics were designed. A flexible and modular strategy was applied for the synthesis of these compounds, enabling diverse access to dramatically simplified rhizopodin-bistramide hybrids. This novel analogue class was analyzed for its antiproliferative and actin binding properties.

PROCESS FOR PREPARING ENANTIOMERICALLY ENRICHED 3-HYDROXYMETHYLPIPERIDINE

The present invention relates to a process for preparing enantiomerically enriched 3-hydroxymethylpiperidine and in particular of the S-enantiomer of (S)-3-hydroxymethyl- piperidine in high chemical and optical purity. The invention also relates to extremely pure (S)-3-hydroxymethylpiperidine and (R)-3-hydroxymethylpiperidine.

FARNESYL PROTEIN TRANSFERASE INHIBITORS

Disclosed are compounds of formula (1.0), wherein R represents a cyclic moiety to which is bound an imodazolylalkyl group; R represents a carbamate, urea, amide or sulfonamide group; and the remaining substituents are as defined herein. Also disclosed is a method of treating cancer and a method of inhibiting farnesyl protein transferase using the disclosed compounds.

FUSED BENZENE DERIVATIVE AND USE

The present invention provides a compound represented by the general formula: [wherein Ring A represents an optionally substituted 5- to 8-membered ring, Ring B represents a further optionally substituted 4- to 10-membered ring, Ring C represents a further optionally substituted benzene ring, X1 represents carbon atom, X2 represents a carbon atom, an oxygen atom, etc., W represents a nitrogen atom, etc., Y11 represents a group represented by the formula CR2R3' (wherein R2 represents a hydrogen atom, a cyano group, a nitro group, etc., and R3' represents a hydrogen atom, a cyano group, a nitro group, etc., respectively), Y21 represents a group represented by the formula CR4R5' (wherein R4 represents a hydrogen atom, a cyano group, a nitro group, etc., and R5' represents a hydrogen atom, a cyano group, a nitro group, etc., respectively), etc., and R1 represents an electron-withdrawing group, respectively. The formula represents a single bond or a double bond] or a salt thereof, which is useful as an androgen receptor modulator.

Novel farnesyl protein transferase inhibitors as antitumor agents

Disclosed are novel tricyclic compounds represented by the formula (1.0): and a pharmaceutically acceptable salt or solvate thereof. The compounds are useful for inhibiting farnesyl protein transferase. Also disclosed are pharmaceutical compositions comprising compounds of formula 1.0. Also disclosed are methods of treating cancer using the compounds of formula 1.0.

Novel farnesyl protein transferase inhibitors as antitumor agents

Disclosed are novel tricyclic compounds represented by the formula (1.0): or a pharmaceutically acceptable salt or solvate thereof. The compounds are useful for inhibiting farnesyl protein transferase. Also disclosed are pharmaceutical compositions comprising compounds of formula 1.0. Also disclosed are methods of treating cancer using the compounds of formula 1.0.

NOVEL AMIDE DERIVATIVES

This invention relates to compounds which are represented by the general formula [I] ???[in which A stands for a group of the following formula [ao] or [b0] ???Ar1, Ar2 and Ar3 stand for optionally substituted phenyl; k stands for 0 or 1; m, n and s stand for 0, 1 or 2; R1 stands for hydrogen or optionally substituted lower alkyl; R2, R3, R4 and R5 either stand for hydrogen or optionally substituted lower alkyl, or R2 and R3, or R4 and R5 together stand for trimethylene and the like; R60 stands for hydrogen, alkyl, or the like; R61and R71 either stand for alkyl and the like, or together stand for trimethylene and the like; X stands for carbonyl or methylene; Y stands for nitrogen or methine; and Q- stands for anion], and the like. The compounds of the invention exhibit selective antagonism to muscarinic M3 receptors, and therefore are useful as safe and effective agents showing little side effect, for treating diseases of the respiratory, urinary and digestive systems.

Stereoselective enzymatic hydrolysis of dimethyl meso-piperidine-3,5-dicarboxylates

Desymmetrization of dimethyl meso-piperidine-3,5-dicarboxylates 3a-c with pig liver esterase (PLE), lipase from Candida cylindracea (CCL) and porcine pancreatic lipase (PPL) is described. The enantioselectivities of the enzymatic transformations and the absolute configurations of the resulting half-esters 2a-c were determined.