(1R,2R,3S,5S,8S)-3-hydroxy-8-methyl-8-azoniabicyclo[3.2.1]octane-2-carboxylic acid chloride

Base Information

• Chemical Name: (1R,2R,3S,5S,8S)-3-hydroxy-8-methyl-8-azoniabicyclo[3.2.1]octane-2-carboxylic acid chloride
• CAS No.: 5796-31-6
• Molecular Formula: C9H15 N O3 . Cl H
• Molecular Weight: 221.684
• Hs Code.: 2933990090
• Mol file: 5796-31-6.mol

Synonyms:(1R,2R,3S,5S,8S)-3-hydroxy-8-methyl-8-azoniabicyclo[3.2.1]octane-2-carboxylic acid chloride

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Chemical Property of (1R,2R,3S,5S,8S)-3-hydroxy-8-methyl-8-azoniabicyclo[3.2.1]octane-2-carboxylic acid chloride

Chemical Property:

• Vapor Pressure: 3.32E-07mmHg at 25°C
• Melting Point: 246°
• Boiling Point: 376.3°C at 760 mmHg
• Flash Point: 181.4°C
• PSA: 60.77000
• LogP: 0.65450
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 221.0818711
• Heavy Atom Count: 14
• Complexity: 231

Purity/Quality:

Safty Information:

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[NH+]1C2CCC1C(C(C2)O)C(=O)O.[Cl-]
• Isomeric SMILES: C[NH+]1[C@H]2CC[C@@H]1[C@H]([C@H](C2)O)C(=O)O.[Cl-]
• Description: Ecgonine (hydrochloride) (Item No. 23314) is an analytical reference standard categorized as a tropane metabolite. Ecgonine is a metabolite of, and a precursor to, cocaine. Ecgonine is regulated as a Schedule II compound in the United States. This product is intended for research and forensic applications.
• Uses: A tropane alkaloid which is both a metabolite and a precursor to Cocaine.

Technology Process of (1R,2R,3S,5S,8S)-3-hydroxy-8-methyl-8-azoniabicyclo[3.2.1]octane-2-carboxylic acid chloride

There total 2 articles about (1R,2R,3S,5S,8S)-3-hydroxy-8-methyl-8-azoniabicyclo[3.2.1]octane-2-carboxylic acid chloride 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 hydrochloride (53-21-4) → ecgonine hydrochloride (5796-31-6)

Guidance literature:

With hydrogenchloride; for 22h; Heating;

DOI:10.1021/ja043935e

Reference yield: 100.0%

Cocaine (50-36-2) → ecgonine hydrochloride (5796-31-6)

Guidance literature:

With hydrogenchloride; Heating;

DOI:10.1002/(SICI)1099-1344(19991230)42:13<1265::AID-JLCR283>3.0.CO;2-Y

Reference yield: 48.0%

benzyl 6-bromohexanoate (78277-26-6) + ecgonine hydrochloride (5796-31-6) → (1R,2R,3S,5S)-3-Hydroxy-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid 5-benzyloxycarbonyl-pentyl ester (173443-25-9)

Guidance literature:

With tetramethyl ammoniumhydroxide; tetraethylammonium iodide; In tetrahydrofuran; N,N-dimethyl-formamide; at 60 ℃; for 20h;

DOI:10.1021/ja043935e

upstream raw materials:

(-)-cocaine hydrochloride

Cocaine

Downstream raw materials:

ecgonine ethyl ester

Ecgonine methyl ester hydrochloride

(1R,2R,3S,5S)-3-Hydroxy-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid 5-benzyloxycarbonyl-pentyl ester

(1R,2R,3S,5S)-3-Benzoyloxy-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid 5-carboxy-pentyl ester