(2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

Base Information

• Chemical Name: (2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
• CAS No.: 481-37-8
• Molecular Formula: C9H15 N O3
• Molecular Weight: 185.223
• European Community (EC) Number: 207-565-4
• Wikipedia: Ecgonine
• ChEMBL ID: CHEMBL612017
• Mol file: 481-37-8.mol

Synonyms:ecgonine;ecgonine acetate, (1R-(exo,exo))-isomer;ecgonine hydrochloride;ecgonine, (1R-(2-endo,3-exo))-isomer

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Chemical Property of (2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 3.32E-07mmHg at 25°C
• Melting Point: 205°C
• Refractive Index: 1.4780 (estimate)
• Boiling Point: 376.3°Cat760mmHg
• PKA: 3.60±0.40(Predicted)
• Flash Point: 181.4°C
• PSA: 60.77000
• Density: 1.293g/cm³
• LogP: -0.14750
• Water Solubility.: 178g/L(temperature not stated)
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 185.10519334
• Heavy Atom Count: 13
• Complexity: 231

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2CCC1C(C(C2)O)C(=O)O
• Isomeric SMILES: CN1C2CCC1[C@H]([C@H](C2)O)C(=O)O

Technology Process of (2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

There total 41 articles about (2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid 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: 100.0%

Cocaine (50-36-2) → ecgonine (481-37-8)

Guidance literature:

With hydrogenchloride; In water; Reflux;

DOI:10.1039/b902863c

Reference yield:

Cocaine (50-36-2) → methanol (67-56-1) + benzoic acid (65-85-0,8013-63-6) + ecgonine (481-37-8) + methyl ecgonine (7143-09-1) + benzylecgonine (519-09-5)

Guidance literature:

With hydrogenchloride; In water; at 70 - 90 ℃; Product distribution; Rate constant; Thermodynamic data; also in plasma and with other reagents ; ΔH_a, ΔS(excit.), Arrhenius parameters;

DOI:10.1002/jps.2600720314

Reference yield:

benzoic acid (65-85-0,8013-63-6) + (+)-pseudoecgonine (481-38-9) → ecgonidine (484-93-5) + ecgonine (481-37-8)

Guidance literature:

at 115 - 120 ℃;

upstream raw materials:

(1R)-2exo-hydroxymethyl-tropane-3exo-ol; hydrochloride

benzoic acid

(+)-pseudoecgonine

benzylecgonine

Downstream raw materials:

ecgonine ethyl ester

(1R)-3exo-trans-cinnamoyloxy-tropane-2exo-carboxylic acid

2,4-diphenyl-cyclobutane-1,3-dicarboxylic acid bis-(2-methoxycarbonyl-tropan-3-yl ester)

anhydroecgonine acid chloride

Refernces

• 1、 Garrett,Seyda. "Prediction of stability in pharmaceutical preparations. XX: Stability evaluation and bioanalysis of cocaine and benzoylecgonine by high-performance liquid chromatography". . p. 258 - 271. Retrieved 1983.
• 2、 Hoepping,George,Flippen-Anderson,Kozikowski. "Radical cyclization strategies for the formation of ring constrained tricyclic tropane analogues". . p. 7427 - 7432. Retrieved 2000.
• 3、 H?seli, Sascha,Holy, Marion,Joksch, Markus,Bergner, Carina,Wree, Andreas,Kurth, Jens,Cankaya, Aylin,Piel, Markus,Krause, Bernd J.,Sitte, Harald H.,R?sch, Frank. "68Ga-Labelled Tropane Analogues for the Visualization of the Dopaminergic System". supporting information. p. 804 - 808. Retrieved 2020/12/15.