5176-22-7

Basic information

• Product Name: 3-Hydroxymethylquinuclidine
• Synonyms: 1-Azabicyclo[2.2.2]octane-3-methanol;3-(Hydroxymethyl)-1-azabicyclo[2.2.2]octane;3-Quinuclidinemethanol;Quinuclidin-3-ylMethanol
• CAS NO: 5176-22-7
• Molecular Formula: C₈H₁₅NO
• Molecular Weight: 141.21
• Mol File: 5176-22-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 114-115℃
• Flash Point: 81.109°C
• Appearance: /
• Density: 1.096g/cm³
• Vapor Pressure: 0.075mmHg at 25°C
• Refractive Index: 1.539
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-Hydroxymethylquinuclidine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxymethylquinuclidine(5176-22-7)
• EPA Substance Registry System: 3-Hydroxymethylquinuclidine(5176-22-7)

Safety Data

• Hazardous Substances Data: 5176-22-7(Hazardous Substances Data)

Usage

General Description

3-Hydroxymethylquinuclidine, also known as 3-HMQ, is a chemical compound with the molecular formula C10H18NO. It is a derivative of quinuclidine and contains a hydroxymethyl group attached to the nitrogen atom of the quinuclidine ring. 3-HMQ is a cholinergic receptor antagonist and has been studied for its potential use in the treatment of neurodegenerative diseases such as Alzheimer's. It has also shown promise as a potential therapeutic agent for the treatment of drug addiction. Additionally, 3-Hydroxymethylquinuclidine has been used in organic synthesis as a versatile building block for the preparation of various pharmaceutical compounds.

InChI:InChI=1/C8H15NO/c10-6-8-5-9-3-1-7(8)2-4-9/h7-8,10H,1-6H2

Upstream product

• 75208-40-1 quinuclidine-3-carboxylic acid 
• 60-29-7 diethyl ether 
• 242810-00-0 3-Methoxymethylquinuclidine-3-ol 
• 5176-21-6 1-azabicyclo[2.2.2]octane-3-carboxaldehyde 
• 6238-33-1 3-quinuclidinecarboxylic acid ethyl ester 

Downstream Products

• 138874-55-2 (3R)-1-azabicyclo[2.2.2]octan-3-ylmethanol 
• 88644-21-7 [(3S)-quinuclidin-3-yl]methanol 
• 138740-84-8 phenoxymethyl-1-aza-bicyclo[2.2.2]octane 
• 64099-45-2 3-chloromethyl-1-azabicyclo[2.2.2]octane 

Relevant articles and documents

PURIFICATION OF 3-ETHOXYCARBONYLQUINUCLIDINE AND ITS CONVERSION TO 3-QUINUCLIDINECARBOXYLIC ACID AND 3-QUINUCLIDINYLMETHANOL

3-Ethoxycarbonylquinuclidine obtained by the Grob method is a mixture of 3-ethoxycarbonyl-1-azabicyclo- and, according to 13C NMR data, 5-ethoxycarbonyl-5-azatricyclo2,7>octanes (about 16:2:1). 3-Ethoxy-carbonylquinuclidine was purified by recrystallization of the hydrochloride, hydrolyzed by water to 3-quinuclidinecarboxylic acid, and reduced by LiAlH4 to 3-quinuclidinylmethanol.

AMINOESTER DERIVATIVES USEFUL IN THE TREATMENT OF COPD

The invention relates to novel compounds which are both phosphodiesterase 4 (PDE4) enzyme inhibitors and muscarinic M3 receptor antagonists, methods of preparing such compounds, compositions containing them and therapeutic use thereof.

Preparation of quinuclidine-3-methanol

A process for the preparation of quinuclidine-3-methanol comprising reacting quinuclidine-3-one acid addition salt with an alkali metal cyanide in an aqueous media to obtain 3-cyano-3-hydroxy-quinuclidine, reacting the latter with anhydrous methanol in the presence of hydrogen chloride gas followed by treatment with aqueous alkali to obtain methyl 3-hydroxy-quinuclidine-3-carboxylate, reacting the latter with thionyl chloride to form methyl 1-azabicyclo(2,2,2)oct-2-ene-3-carboxylate, hydrogenating the latter with Raney nickel to obtain methyl 1-azabicyclo(2,2,2)octane-3-carboxylate and reducing the latter to obtain quinuclidine-3-methanol which is an intermediate for mequitazine which is useful as an antihistaminic.