(1R,3S,5S)-3'-hydroxy-2'-phenylpropionic acid 8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl ester

Base Information

• Chemical Name: (1R,3S,5S)-3'-hydroxy-2'-phenylpropionic acid 8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl ester
• CAS No.: 22150-33-0
• Molecular Formula: C₁₇H₂₁NO₃
• Molecular Weight: 287.359
• Mol file: 22150-33-0.mol

Synonyms:(1R,3S,5S)-3'-hydroxy-2'-phenylpropionic acid 8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl ester

Chemical Property of (1R,3S,5S)-3'-hydroxy-2'-phenylpropionic acid 8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S,5S)-3'-hydroxy-2'-phenylpropionic acid 8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl ester

There total 11 articles about (1R,3S,5S)-3'-hydroxy-2'-phenylpropionic acid 8-methyl-8-azabicyclo[3.2.1]oct-6-en-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: 96.0%

scopolamine (51-34-3,138-12-5,64069-63-2,124917-17-5) → (αS)-α-(hydroxymethyl)benzeneacetic acid (endo)-8-methyl8-azabicyclo[3.2.1]oct-6-en-3-yl ester (22150-33-0,54725-48-3,61616-97-5)

Guidance literature:

With ethanol; copper; zinc;

DOI:10.1016/j.bmcl.2003.09.081

Reference yield: 88.0%

scopolamine hydrobromide trihydrate (152612-85-6) → (αS)-α-(hydroxymethyl)benzeneacetic acid (endo)-8-methyl8-azabicyclo[3.2.1]oct-6-en-3-yl ester (22150-33-0,54725-48-3,61616-97-5)

Guidance literature:

With zinc/copper couple; In ethanol; for 16h; Reflux;

Reference yield: 85.0%

(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ol (20513-09-1) + (αS)-α-(acetoxymethyl)benzeneacetyl chloride (183626-74-6) → (αS)-α-(hydroxymethyl)benzeneacetic acid (endo)-8-methyl8-azabicyclo[3.2.1]oct-6-en-3-yl ester (22150-33-0,54725-48-3,61616-97-5)

Guidance literature:

(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ol; With toluene-4-sulfonic acid; In diethyl ether; at 20 ℃; for 0.666667h;

(αS)-α-(acetoxymethyl)benzeneacetyl chloride; In benzene; at 82 ℃; for 2.5h;

With hydrogenchloride; In benzene; at 20 ℃; for 12h;

DOI:10.1002/hlca.200390258

upstream raw materials:

trop-6-ene-3endo-ol; hydrochloride

scopolamine

(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ol

(αS)-α-(acetoxymethyl)benzeneacetyl chloride

Downstream raw materials:

scopolamine

(1S,3R,5S)-8-Methyl-8-aza-bicyclo[3.2.1]octane-1,3-diol

N-demethyltiotropium

(1R,3S,5S)-2'-hydroxy-2',2'-di(thiophen-2''-yl)acetic acid 8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl ester

Refernces

• 1、 -. "FLUOROPHENYL SUBSTITUTED MUSCARINIC RECEPTOR LIGANDS WITH SELECTIVITY FOR M3 OVER M2". Page/Page column 35; 36. . Retrieved 2019/06/23.
• 2、 Issa, Fatiah,Kassiou, Michael,Chan, Hak-Kim,McLeod, Malcolm D.. "Synthesis and radiolabelling of ipratropium and tiotropium for use as PET ligands in the study of inhaled drug deposition". . p. 53 - 58. Retrieved 2007/10/03.