Methyl 8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylate

Base Information

• Chemical Name: Methyl 8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylate
• CAS No.: 36127-17-0
• Molecular Formula: C10H10N2O4S
• Molecular Weight: 197.234
• NSC Number: 72911
• DSSTox Substance ID: DTXSID00957545
• Nikkaji Number: J695.152J
• Wikipedia: 2-Carbomethoxytropinone
• Mol file: 36127-17-0.mol

Synonyms:36127-17-0;Methyl 8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylate;2-carbomethoxy-3-tropinone;112574-77-3;8-Methyl-3-oxo-8-azabicyclo[3.2.1]octan-2-carboxylic acid Methyl ester;117203-92-6;NSC72911;2-Carbomethoxytropinone;NCIOpen2_000597;2-(Carbomethoxy)-3-tropinone;SCHEMBL1012062;2-(Methoxycarbonyl)-3-tropinone;DTXSID00957545;NSC-72911;AKOS015919937;CS-W005990;DS-12687;FT-0639299;A823133;Methyl 8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylate #;3-Oxo-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid methyl ester;8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylic acid methyl ester

Chemical Property of Methyl 8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylate

Chemical Property:

• Vapor Pressure: 0.00166mmHg at 25°C
• Melting Point: 104℃ (approx)
• Refractive Index: 1.502
• Boiling Point: 294.108 °C at 760 mmHg
• PKA: 10.89±0.20(Predicted)
• Flash Point: 131.672 °C
• PSA: 46.61000
• Density: 1.173 g/cm³
• LogP: 0.14910
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 197.10519334
• Heavy Atom Count: 14
• Complexity: 277

Purity/Quality:

99% ^*data from raw suppliers

2-(Methoxycarbonyl)-3-tropinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2CCC1C(C(=O)C2)C(=O)OC
• Description: 2-Carbomethoxy-3-tropinone is an advanced intermediate in the biosynthesis of cocaine.
• Uses: 2-carbomethoxy-3-tropinone is an intermediate in the synthesis of cocaine isomers at the cocaine receptor.

Technology Process of Methyl 8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylate

There total 16 articles about Methyl 8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylate 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: 89.0%

tropinone (532-24-1) + carbonic acid dimethyl ester (616-38-6) → methyl 8-methyl-3-oxo-8-azabicyclo<3.2.1>octan-2-carboxylate (36127-17-0,53955-90-1,85506-18-9,112574-77-3,112652-64-9,145414-58-0,149197-42-2)

Guidance literature:

carbonic acid dimethyl ester; With sodium hydride; In cyclohexane; at 70 ℃; Inert atmosphere;

tropinone; In cyclohexane; Reflux; Inert atmosphere;

Reference yield: 80.0%

tropinone (532-24-1) + carbonic acid dimethyl ester (616-38-6) → (+/-)-2-(carbomethoxy)-3-tropinone (36127-17-0)

Guidance literature:

With methanol; sodium hydride; In cyclohexane; for 1.75h; Heating;

DOI:10.1021/jo00340a004

Reference yield: 55.0%

3-oxo-tropane-2,4-dicarboxylic acid dimethyl ester (100371-46-8) → (+/-)-2-(carbomethoxy)-3-tropinone (36127-17-0) + tropinone (532-24-1)

Guidance literature:

With phosphate buffer; In water; at 20 ℃; for 24h; pH=8.0;

DOI:10.1016/S0040-4039(99)00976-4

upstream raw materials:

butanedial

acetone-1,3-dicarboxylic acid mono-methyl ester

methylamine hydrochloride

tropinone

Downstream raw materials:

methyl (endo, endo)-3-hydroxy-8-methyl-8-azabicyclo<3.2.1>octan-2-carboxylate

methyl (2-endo, 3-exo)-3-hydroxy-8-methyl-8-azabicyclo<3.2.1>octan-2-carboxylate

cocaine

pseudotropine

Refernces

• 1、 Remen, L'ubos,Bezencon, Olivier,Richard-Bildstein, Sylvia,Bur, Daniel,Prade, Lars,Corminboeuf, Olivier,Boss, Christoph,Grisostomi, Corinna,Sifferlen, Thierry,Strickner, Panja,Hess, Patrick,Delahaye, Stephane,Treiber, Alexander,Weller, Thomas,Binkert, Christoph,Steiner, Beat,Fischli, Walter. "New classes of potent and bioavailable human renin inhibitors". body text. p. 6762 - 6765. Retrieved 2010/06/12.
• 2、 Node, Manabu,Nakamura, Soichi,Nakamura, Daisaku,Katoh, Takahiro,Nishide, Kiyoharu. "Novel asymmetric dealkoxycarbonylation of 3-oxo-8-azabicyclo[3.2.1]- octane-2,4-dicarboxylates using porcine liver esterase: A new route to (-)- anhydroecgonine methyl ester". . p. 5357 - 5360. Retrieved 2007/10/03.