59653-42-8

Basic information

• Product Name: 1-Azabicyclo[2.2.2]octan-3-ol, acetate (ester), (S)-
• CAS NO: 59653-42-8
• Molecular Formula: C9H15NO2
• Molecular Weight: 169.224
• Mol File: 59653-42-8.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: 1-Azabicyclo[2.2.2]octan-3-ol, acetate (ester), (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Azabicyclo[2.2.2]octan-3-ol, acetate (ester), (S)-(59653-42-8)
• EPA Substance Registry System: 1-Azabicyclo[2.2.2]octan-3-ol, acetate (ester), (S)-(59653-42-8)

Safety Data

• Hazardous Substances Data: 59653-42-8(Hazardous Substances Data)

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 
• 34286-16-3 2-ethoxycarbonyl-3-quinuclidinone 
• 1838-39-7 ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate 
• 1193-65-3 3-quinuclidinone hydrochloride 

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⁺⁾ 
• 25333-42-0 (R)-quinuclidin-3-ol 
• 3684-26-2 (S)-quinuclidin-3-ol 
• 142999-61-9 (S)-N-(S)-1-Aza-bicyclo[2.2.2]oct-3-yl-3,3,3-trifluoro-2-methoxy-2-phenyl-propionamide 

Relevant articles and documents

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.

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.

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.