(1R,2S,3S,5S)-3-(4-Chlorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid, methyl ester

Base Information

• Chemical Name: (1R,2S,3S,5S)-3-(4-Chlorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid, methyl ester
• CAS No.: 130342-80-2
• Molecular Formula: C16H20 Cl N O2
• Molecular Weight: 293.793
• Nikkaji Number: J1.254.609B,J424.759K,J328.920F
• Wikipedia: RTI-31
• Mol file: 130342-80-2.mol

Synonyms:3-(4-chlorophenyl)tropane-2-carboxylic acid methyl ester;RTI-COC 31;RTI-COC-31

Chemical Property of (1R,2S,3S,5S)-3-(4-Chlorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid, methyl ester

Chemical Property:

• Vapor Pressure: 7.55E-06mmHg at 25°C
• Boiling Point: 375.9°Cat760mmHg
• Flash Point: 181.1°C
• PSA: 29.54000
• Density: 1.185g/cm³
• LogP: 3.01720
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 293.1182566
• Heavy Atom Count: 20
• Complexity: 368

Purity/Quality:

99%, ^*data from raw suppliers

RTI-31 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2CCC1C(C(C2)C3=CC=C(C=C3)Cl)C(=O)OC
• Isomeric SMILES: CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)C3=CC=C(C=C3)Cl)C(=O)OC
• Description: RTI-31 (Item No. 17977) is an analytical reference standard that is categorized as a tropane. RTI-31 increases self-administration in rhesus monkeys. This product is intended for research and forensic applications.

Technology Process of (1R,2S,3S,5S)-3-(4-Chlorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid, methyl ester

There total 18 articles about (1R,2S,3S,5S)-3-(4-Chlorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid, methyl 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%

(4-chlorphenyl)magnesium bromide (873-77-8) + methyl ecgonidine (50373-10-9) → 2β-carbomethoxy-3β-(4-chlorophenyl)tropane (130342-80-2) + 2α-carbomethoxy-3β-(4'-chlorophenyl)tropane (173830-21-2)

Guidance literature:

In diethyl ether; dichloromethane; at -40 ℃; for 3.5h;

DOI:10.1002/jhet.5570330676

Reference yield: 49.0%

(4-chlorphenyl)magnesium bromide (873-77-8) + methyl ecgonidine (50373-10-9) → 2β-carbomethoxy-3β-(4-chlorophenyl)tropane (130342-80-2)

Guidance literature:

In diethyl ether; at -40 ℃; for 2h;

DOI:10.1021/jm0101904

Reference yield: 44.0%

(4-chlorphenyl)magnesium bromide (873-77-8) + methyl ecgonidine (50373-10-9) → 2β-carbomethoxy-3β-(4-chlorophenyl)tropane (130342-80-2) + 3α-(4-chlorophenyl)tropane-2β-carboxylic acid methyl ester (184376-54-3)

Guidance literature:

(4-chlorphenyl)magnesium bromide; methyl ecgonidine; In diethyl ether; dichloromethane; at -50 ℃; for 3h; Inert atmosphere;

With trifluoroacetic acid; In diethyl ether; dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/jlcr.3905

upstream raw materials:

(R)-(-)-anhydroecgonine methyl ester

(4-chlorphenyl)magnesium bromide

methyl ecgonidine

(-)-cocaine hydrochloride

Downstream raw materials:

β-CPPIT

N-[4-(4-aminophenyl)butyl]-2β-carbomethoxy-3β-(4-chlorophenyl)tropane

N-[4-(4-nitrophenyl)butyl]-2β-carbomethoxy-3β-(4-chlorophenyl)tropane

N-[4-(3-iodo-4-aminophenyl)butyl]-2β-carbomethoxy-3β-(4-chlorophenyl)tropane

Refernces

• 1、 Xu,Trudell. "Stereoselective synthesis of 2β-carbomethoxy-3β-phenyltropane derivatives. Enhanced stereoselectivity observed for the conjugate addition reaction of phenylmagnesium bromide derivatives with anhydro dichloromethane". . p. 2037 - 2039. Retrieved 1996.
• 2、 -. "Method for preparing organoboron derivative containing oxygen and aromatic ring as labeled precursor of dopamine positron emission tomography imaging agent". Paragraph 2; 4. . Retrieved 2021/03/04.