1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

Base Information

• Chemical Name: 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester
• CAS No.: 1026791-31-0
• Molecular Formula: C₂₁H₂₉NO₂
• Molecular Weight: 327.467
• Mol file: 1026791-31-0.mol

Synonyms:1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

Chemical Property of 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

There total 11 articles about 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester 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: 70.0%

1-phenyl-1-cycloheptanecarboxylic acid (7086-29-5) + (R)-quinuclidin-3-ol (25333-42-0) → 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (1026791-31-0)

Guidance literature:

With sodium hydride; In toluene; Reflux;

DOI:10.1016/j.bmcl.2013.09.092

Reference yield:

cycloheptanone (502-42-1) → 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (1026791-31-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: iodine; magnesium / tetrahydrofuran / 0.33 h / Inert atmosphere; Reflux

1.2: 0.17 h

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.08 h / 60 °C

2.2: 60 °C / Reflux

3.1: potassium; sodium / diethyl ether / 20 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

3.3: pH 7

4.1: trimethylsilyldiazomethane / toluene / 0.75 h / Inert atmosphere

5.1: toluene / 0.5 h / Reflux

5.2: Inert atmosphere; Reflux

With iodine; sodium; potassium; sodium hydride; magnesium; trimethylsilyldiazomethane; In tetrahydrofuran; diethyl ether; toluene; mineral oil;

Reference yield:

methyl 1-phenylcycloheptanecarboxylate (94163-02-7) + (R)-quinuclidin-3-ol (25333-42-0) → 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (1026791-31-0)

Guidance literature:

With sodium; In n-heptane; toluene; for 96h; Heating / reflux;

upstream raw materials:

methyl 1-phenylcycloheptanecarboxylate

(R)-quinuclidin-3-ol

cycloheptanecarbonitrile

cycloheptanone

Downstream raw materials:

3(R)-1-benzyl-3-{[(1-phenylcycloheptyl)carbonyl]oxy}-1-azoniabicyclo[2.2.2]octane bromide

3(R)-1-(3-methoxybenzyl)-3-{[(1-phenylcycloheptyl)carbonyl]oxy}-1-azoniabicyclo[2.2.2]octane bromide

3(R)-1-methyl-3-{[(1-phenylcycloheptyl)carbonyl]oxy}-1-azoniabicyclo[2.2.2]octane iodide

3(R)-1-(4-fluorobenzyl)-3-{[(1-phenylcycloheptyl)carbonyl]oxy}-1-azoniabicyclo[2.2.2]octane bromide

Refernces

• 1、 -. "QUINUCLIDINE DERIVATIVES AS MUSCARINIC M3 RECEPTOR ANTAGONISTS". Page/Page column 21. . Retrieved 2011/08/02.
• 2、 -. "QUINUCLIDINE DERIVATIVES AND THEIR USE AS MUSCARINIC RECEPTOR ANTAGONISTS FOR THE TREATMENT OF ASTHMA AND CHRONIC OBSTRUCTIVE PULMONARY DISEASE (COPD)". Page/Page column 40-41. . Retrieved 2009/12/23.