[(3R)-1-azabicyclo[2.2.2]octan-3-yl] acetate

Base Information

• Chemical Name: [(3R)-1-azabicyclo[2.2.2]octan-3-yl] acetate
• CAS No.: 59653-40-6
• Molecular Formula: C9H15NO2
• Molecular Weight: 169.224
• UNII: 9FV0LA67OF
• Nikkaji Number: J550.179B
• ChEMBL ID: CHEMBL612034
• Mol file: 59653-40-6.mol

Synonyms:59653-40-6;(R) aceclidine;1-Azabicyclo[2.2.2]octan-3-ol, 3-acetate, (3R)-;Aceclidine, (R)-;[(3R)-1-azabicyclo[2.2.2]octan-3-yl] acetate;(R)-3-Acetoxyquinuclidine;9FV0LA67OF;(R)-quinuclidin-3-yl acetate;1-Azabicyclo(2.2.2)octan-3-ol, 3-acetate, (3R)-;1-Azabicyclo(2.2.2)octan-3-ol, acetate (ester), (R)-;(?)-Aceclidine;(R)-ACECLIDINE;UNII-9FV0LA67OF;1-Azabicyclo[2.2.2]octan-3-ol,3-acetate,(3R)-;CHEMBL612034;SCHEMBL9146752;BDBM50478153;PDSP1_000690;PDSP2_000680;NCGC00485382-01

Chemical Property of [(3R)-1-azabicyclo[2.2.2]octan-3-yl] acetate

Chemical Property:

• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 169.110278721
• Heavy Atom Count: 12
• Complexity: 185

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CN2CCC1CC2
• Isomeric SMILES: CC(=O)O[C@H]1CN2CCC1CC2

Technology Process of [(3R)-1-azabicyclo[2.2.2]octan-3-yl] acetate

There total 7 articles about [(3R)-1-azabicyclo[2.2.2]octan-3-yl] acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

acetic anhydride (108-24-7) + 3-quinuclidinol (1619-34-7) → 3-acetoxyquinuclidine (827-61-2,59653-40-6,59653-42-8,72353-53-8)

Guidance literature:

for 4h; Heating;

DOI:10.1080/00397919208021320

Reference yield:

3-quinuclidinol (1619-34-7) → 3-acetoxyquinuclidine (827-61-2,59653-40-6,59653-42-8,72353-53-8)

Guidance literature:

With acetic anhydride; In pyridine; water;

Reference yield:

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 3-acetoxyquinuclidine (827-61-2,59653-40-6,59653-42-8,72353-53-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium tert-butylate / toluene / 4.5 h / Reflux; Inert atmosphere

2.1: Reflux

2.2: 20 °C

3.1: sodium hydroxide; water / 0.5 h / -5 - 0 °C

3.2: 1.5 h

4.1: 2 h / 20 °C

With potassium tert-butylate; water; sodium hydroxide; In toluene; 1.1: |Dieckmann Condensation;

upstream raw materials:

acetic anhydride

3-quinuclidinol

3-Acetoxy-1-(2-methyl-acryloyloxymethyl)-1-azonia-bicyclo[2.2.2]octane; chloride

3-quinuclidinone hydrochloride

Downstream raw materials:

p-methylbenzoyloxymethyl-3-acetoxyquinuclidinium chloride

p-chlorobenzoyloxymethyl-3-acetoxyquinuclidinium chloride

m-nitrobenzoyloxymethyl-3-acetoxyquinuclidinium chloride

1-(phenylacetoxy)-3-acetoxyquinuclidinium chloride