methyl (1R,2S,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate Pseudococaine

Base Information

• Chemical Name: methyl (1R,2S,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate Pseudococaine
• CAS No.: 478-73-9
• Molecular Formula: C17H21 N O4
• Molecular Weight: 303.358
• Mol file: 478-73-9.mol

Synonyms:1aH,5aH-Tropane-2a-carboxylic acid, 3b-hydroxy-, methyl ester, benzoate (ester) (8CI);8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, methylester, [1R-(2-endo,3-exo)]-; Pseudococaine (6CI,7CI); (+)-Pseudococaine;(R)-Pseudococaine; 2a-Carbomethoxy-3b-benzoyloxytropane; Delcaine; Depsococaine; Dextrocaine; Isocaine;Isococain; Isococaine; d-Pseudococaine; d-y-Cocaine

Chemical Property of methyl (1R,2S,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate Pseudococaine

Chemical Property:

• Vapor Pressure: 1.87E-06mmHg at 25°C
• Melting Point: 47°
• Boiling Point: 395.2°Cat760mmHg
• Flash Point: 192.8°C
• PSA: 55.84000
• Density: 1.22g/cm³
• LogP: 1.80560

Purity/Quality:

99%, ^*data from raw suppliers

PSEUDOCOCAINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl (1R,2S,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate Pseudococaine

There total 9 articles about methyl (1R,2S,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate Pseudococaine 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: 66.0%

benzoyl chloride (98-88-4) + methyl (1R,2S,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate hydrochloride (38969-40-3,65027-05-6,79735-03-8,93738-78-4,93738-79-5,112574-29-5,112652-63-8,131722-69-5) → (+)-pseudococaine (478-73-9)

Guidance literature:

benzoyl chloride; methyl (1R,2S,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate hydrochloride; With dmap; triethylamine; In dichloromethane; at 20 ℃; for 12h; Inert atmosphere;

With sodium hydroxide; In dichloromethane; water;

DOI:10.1021/ol3020607

Reference yield:

benzoyl chloride (98-88-4) → (+/-)-allococaine (50-36-2,478-73-9,518-97-8,668-19-9,7058-74-4,21030-42-2,21030-43-3,21030-44-4,21206-60-0,47195-07-3,85354-45-6,131722-66-2,131829-33-9)

Guidance literature:

With pyridine;

DOI:10.1021/jo01092a040

Reference yield:

→ (+/-)-allococaine (50-36-2,478-73-9,518-97-8,668-19-9,7058-74-4,21030-42-2,21030-43-3,21030-44-4,21206-60-0,47195-07-3,85354-45-6,131722-66-2,131829-33-9)

Guidance literature:

rac-Allopseudoecgonin-methylester, 1.) Benzoylchlorid, 2.) K2CO3;

upstream raw materials:

(+/-)-pseudococaine

benzoyl chloride

tert-butyl (1R,2S,3R,4R,5S)-3-hydroxy-4-iodo-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

tert-butyl (1R,2S,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Downstream raw materials:

ecgonidine

(S)-pseudoecgonine methyl ester

methyl (1R,2S,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

(1R)-3exo-benzoyloxy-tropane-2endo-carboxylic acid

Refernces

• 1、 Simoni, Daniele,Roberti, Marinella,Andrisano, Vincenza,Manferdini, Monica,Rondanin, Riccardo,Invidiata, Francesco Paolo. "Two-carbon bridge substituted cocaines: Enantioselective synthesis, attribution of the absolute configuration and biological activity of novel 6- and 7-methoxylated cocaines". . p. 275 - 287. Retrieved 2007/10/03.
• 2、 Carroll, F. Ivy,Coleman, Michael L.,Lewin, Anita H.. "Syntheses and Conformational Analyses of Isomeric Cocaines: A Proton and Carbon-13 Nuclear Magnetic Resonance Study". . p. 13 - 19. Retrieved 2007/10/02.