59653-40-6

Usage

Uses

Used in Pharmaceutical Industry:
1-Azabicyclo[2.2.2]octan-3-ol, acetate (ester), (R)is used as a chiral building block for the synthesis of various drugs and pharmaceuticals. Its unique structure allows for the creation of enantiomerically pure compounds, which is crucial in ensuring the desired therapeutic effects and minimizing potential side effects.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 1-Azabicyclo[2.2.2]octan-3-ol, acetate (ester), (R)is utilized in the development of new drugs for neurological and psychiatric disorders. Its chiral properties enable the design of more effective and targeted treatments, addressing the specific needs of these complex conditions.
Used in Chromatography:
1-Azabicyclo[2.2.2]octan-3-ol, acetate (ester), (R)is employed as a chiral resolving agent in chromatography. This application leverages its ability to selectively interact with enantiomers, facilitating the separation and analysis of chiral compounds, which is essential in various chemical and pharmaceutical processes.
Used in Asymmetric Catalysis:
As a ligand in asymmetric catalysis, 1-Azabicyclo[2.2.2]octan-3-ol, acetate (ester), (R)plays a significant role in enhancing the selectivity and efficiency of catalytic reactions. This contributes to the production of enantiomerically pure products, which is particularly important in the synthesis of pharmaceuticals and other specialty chemicals.

Upstream product

• 108-24-7 acetic anhydride 
• 1619-34-7 3-quinuclidinol 
• 76656-18-3 3-Acetoxy-1-(2-methyl-acryloyloxymethyl)-1-azonia-bicyclo[2.2.2]octane; chloride 
• 1193-65-3 3-quinuclidinone hydrochloride 
• 1838-39-7 ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate 
• 34286-16-3 2-ethoxycarbonyl-3-quinuclidinone 

Downstream Products

• 75447-70-0 p-methylbenzoyloxymethyl-3-acetoxyquinuclidinium chloride 
• 75447-73-3 p-chlorobenzoyloxymethyl-3-acetoxyquinuclidinium chloride 
• 75447-72-2 m-nitrobenzoyloxymethyl-3-acetoxyquinuclidinium chloride 
• 73360-17-5 1-(phenylacetoxy)-3-acetoxyquinuclidinium chloride 
• 75447-75-5 p-nitrobenzoyloxymethyl-3-acetoxyquinuclidinium chloride 
• 73360-13-1 1-<(benzyloxy)methyl>-3-acetoxyquinuclidinium bromide 
• 73360-21-1 1-benzyl-3-acetoxyquinuclidinium chloride 
• 75447-74-4 p-bromobenzoyloxymethyl-3-acetoxyquinuclidinium chloride 
• 75447-71-1 m-bromobenzoyloxymethyl-3-acetoxyquinuclidinium chloride 
• 75447-69-7 1-p-methoxybenzoyloxymethyl-3-acetoxyquinuclidinium chloride 
• 41967-35-5 Br^(1-)*C₁₆H₂₂NO₂⁽¹⁺⁾ 
• 320347-97-5 hydroxydithien-2-ylacetic acid 1-aza-bicyclo[2.2.2]oct-3(R)-yl ester 
• 142999-61-9 (S)-N-(S)-1-Aza-bicyclo[2.2.2]oct-3-yl-3,3,3-trifluoro-2-methoxy-2-phenyl-propionamide 
• 6530-09-2 (S)-1-azabicyclo[2.2.2]oct-3-ylamine dihydrochloride 

Relevant academic research and scientific papers

Preparation method of optical activity 3-quinuclidinol

The invention relates to an intermediate synthesis method, belongs to the field of organic synthesis, and particularly relates to a preparation method of optical activity 3-quinuclidinol with the advantages that the operation is simple and convenient, the cost is low, and the method is suitable for industrial production. An intermediate of 3-quinuclidinol is obtained by using 4-nipecotic acid as astarting material through esterification, nucleophilic substitution, Dieckmann condensation, decarboxylation, salification, reduction, acetylization, chemical resolution and the like. The reaction formula is shown in the description.

PHARMACEUTICAL COMPOSITION FOR USE IN MEDICAL AND VETERINARY OPHTHALMOLOGY

The invention relates to pharmaceutics, medicine, in particular to manufacturing and use of pharmaceutical compositions of medicines (ophthalmic preparations) comprising mitochondria-addressed antioxidant and a set of auxiliary substances providing effective treatment for ophtalmological diseases in humans and animals.

Stereoselective synthesis of the optical isomers of a new muscarinic receptor antagonist, quinuclidin-3-yl 2-(cyclopent-1-enyl)-2-hydroxy-2- phenylacetate

The enantiopure isomers of a new muscarinic receptor antagonist, quinuclidin-3-yl 2-(cyclopent-1-enyl)-2-hydroxy-2-phenylacetate were synthesised by a practical stereoselective synthetic method, using pivaldehyde as steric hindrance agent from the chiral starting material, (S) or (R)-mandelic acid. The isomers were obtained with 72-78% yields in 98-99% e.e.

Synthesis of the optical isomers of a new anticholinergic drug, penehyclidine hydrochloride (8018)

A practical diastereoselective synthetic method for 8018 enantiopure isomers is described. The intramolecular asymmetric epoxidation of mono-sulfonate 4 was applied for the execution of the synthesis of the key chiral building block for the first time. The isomers were obtained with 70-76% yields in 99-100% ee.

A practical chemoenzymatic process to access (R)-quinuclidin-3-ol on scale

(±)-3-Butyryloxyquinuclidinium butyrate 6 (2 M, 571 g/L), prepared from (±)-quinuclidin-3-ol 1 and butyric anhydride, undergoes enantioselective hydrolysis by an Aspergillus melleus protease {1.0% (w/v)} in water in the presence of Ca(OH)2 to keep the reaction at pH 7 and trap butyric acid that is introduced as part of (±)-6 and generated by the enzymatic hydrolysis. After a 24 h period, extraction with n-heptane provides (R)-quinuclidin-3-yl butyrate 5a, which, on methanolysis with Na2CO3, is converted into (R)-1, a common pharmacophore of neuromodulators acting on muscarinic receptors, in 96% ee and 42% overall yield from (±)-1. The unwanted antipode (S)-1, which is extracted into n-butanol and purified via its hydrochloride salt in 89% ee and 40% overall yield from (±)-1, can be racemized by the catalysis of Raney Co at 140°C under an atmosphere of H2 (5 kg/cm2) to regenerate (±)-1 in 97% yield.

Boronic acid adducts of rhenium dioxime and technetium-99m dioxime complexes containing a biochemically active group

Boronic acid adducts of technetium-99m and radioactive rhenium dioxime complexes, each of which include biochemically active groups, are useful as diagnostic and therapeutic agents, respectively.

Synthesis of (R) and (S)-3-aminoquinuclidine from 3-quinuclidinone and (S) and (R)-1-phenethylamine

The synthesis of (R) and (S)-3-amino quinuclidine, an important building block for the synthesis of chiral 5-HT3 serotonin receptor antagonists, is described. The key reaction is the reduction by NaBH4 of the imine prepared from the 3-quinuclidinone and chiral (S) or (R)-1-phenethylamine.

Soft drugs. 2. Soft alkylating compounds as potential antitumor agents.

A class of soft alkylating compounds as potential anticancer agents was developed. The first examples include alpha-halo esters of various carboxylic acids. A new method for quantitative evaluation of the alkylating reactivity was developed, using a competitive alkylation reactivity was developed, using a competitive alkylation reaction, followed by NMR analysis of the reaction mixture. The method is sensitive and reproducible. One of the two selected soft alkylating agents, chloromethyl hexanoate, was found to have anticancer activity.

Process for preparing quinuclidine enantiomers

A new composition of matter, (+) 3-acetoxy- quinuclidine and its salts, ophthalmic compositions comprising this compound or any of its physiologically acceptable salts in a suitable carrier such as a phosphate buffer, and a process of preparation of the active ingredients, which comprises esterifying quinuclidinol so as to obtain racemic 3-lower-alkoxy quinuclidine, subjecting same to enzymatic hydrolysis by a cholinesterase so as to selectively hydrolyze the (-) isomer, separating the unchanged (+) lower-alkoxy quinuclidine, hydrolyzing the latter and esterifying it to the desired compound. Amongst various homolophes the preferred compound is (+)3-acetoxy quinuclidine as this is pharmaceutically the most potent one.