Bis[(1r,2r,3s,5s)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 2,4-diphenylcyclobutane-1,3-dicarboxylate

Base Information

• Chemical Name: Bis[(1r,2r,3s,5s)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 2,4-diphenylcyclobutane-1,3-dicarboxylate
• CAS No.: 490-17-5
• Molecular Formula: C38H46N2O8
• Molecular Weight: 658.792
• European Community (EC) Number: 207-707-5
• UNII: V7VU89LP2K
• DSSTox Substance ID: DTXSID90883400
• Mol file: 490-17-5.mol

Synonyms:490-17-5;a-Truxilline;Truxilline, alpha-;V7VU89LP2K;bis[(1r,2r,3s,5s)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 2,4-diphenylcyclobutane-1,3-dicarboxylate;Bis[(1R,2R,3S,5S)-2-methoxycarbonyl-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 2,4-diphenylcyclobutane-1,3-dicarboxylate;Bis[2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 2,4-diphenylcyclobutane-1,3-dicarboxylate, stereoisomer;Cocamine;1,3-CYCLOBUTANEDICARBOXYLIC ACID, 2,4-DIPHENYL-, 1,3-BIS((1R,2R,3S,5S)-2-(METHOXYCARBONYL)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL) ESTER, (1.ALPHA.,2.ALPHA.,3.BETA.,4.BETA.)-;1,3-Cyclobutanedicarboxylic acid, 2,4-diphenyl-, 1,3-bis[(1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] ester, (1.alpha.,2.alpha.,3.beta.,4.beta.)-;Bis(2-(methoxycarbonyl)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl) 2,4-diphenylcyclobutane-1,3-dicarboxylate, stereoisomer;EINECS 207-707-5;.ALPHA.-TRUXILLIN;UNII-V7VU89LP2K;TRUXILLINE, .ALPHA.-;.GAMMA.-ISOATROPYLCOCAINE;DTXSID90883400;AKOS040734851;COCAINE HYDROCHLORIDE IMPURITY B [EP IMPURITY];1,3-Cyclobutanedicarboxylic acid, 2,4-diphenyl-, 1,3-bis((1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl) ester, (1alpha,2alpha,3beta,4beta)-;1,3-Cyclobutanedicarboxylic acid, 2,4-diphenyl-, bis((1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl) ester, (1alpha,2alpha,3beta,4beta)-;1,3-Cyclobutanedicarboxylic acid, 2,4-diphenyl-, bis[(1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] ester, (1.alpha.,2.alpha.,3.beta.,4.beta.)-;BIS((1R,2R,3S,5S)-2-(METHOXYCARBONYL)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL) (1R,2C,3T,4T)-2,4-DIPHENYLCYCLOBUTANE-1,3-DICARBOXYLATE

Chemical Property of Bis[(1r,2r,3s,5s)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 2,4-diphenylcyclobutane-1,3-dicarboxylate

Chemical Property:

• Melting Point: 80°C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 111.68000
• Density: 1.29g/cm³
• LogP: 3.81080
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 12
• Exact Mass: 658.32541643
• Heavy Atom Count: 48
• Complexity: 1110

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2CCC1C(C(C2)OC(=O)C3C(C(C3C4=CC=CC=C4)C(=O)OC5CC6CCC(C5C(=O)OC)N6C)C7=CC=CC=C7)C(=O)OC
• Isomeric SMILES: CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)C3C(C(C3C4=CC=CC=C4)C(=O)O[C@H]5C[C@@H]6CC[C@H]([C@H]5C(=O)OC)N6C)C7=CC=CC=C7)C(=O)OC
• Description: From the leaves of Erythroxylon truxillense Rusby, Hesse isolated an amorphous alkaloid which he designated Cocamine. This was subsequently shown by Liebermann to be a mixture of two isomeric bases and, although the pure alkaloids have not yet been obtained from the alkaloidal mixture owing to difficulties in their separation, each has been prepared synthetically. This particular alkaloid is an amorphous white powder which is soluble in all organic solvents except light petroleum and also insoluble in H20. Solutions of the base are alllaevorotatory and have an intensely bitter taste. Acid hydrolysis with dilute HCl yields MeOH, (-)-ecgonine and Q-truxillic acid, m.p. 228°C. The alkaloid is synthesized by the action of α-truxillic anhydride on (-)-ecgonine followed by methylation of the resulting α-truxilloylecgonine.

Technology Process of Bis[(1r,2r,3s,5s)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 2,4-diphenylcyclobutane-1,3-dicarboxylate

There total 3 articles about Bis[(1r,2r,3s,5s)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 2,4-diphenylcyclobutane-1,3-dicarboxylate 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:

ecgonine (481-37-8) + γ-truxillic anhydride (2898-38-6,37518-25-5) → 2,4-diphenyl-cyclobutane-1,3-dicarboxylic acid bis-(2-methoxycarbonyl-tropan-3-yl ester) (490-17-5,113350-55-3,113351-64-7)

Guidance literature:

With water; at 100 ℃; γ-truxillic acid bis-<2-methoxycarbonyl-tropyl ester>; Behandeln des Reaktionsprodukts mit methylalkoholischer Salzsaeure;

Reference yield:

truxillic acid (490-20-0) → 2,4-diphenyl-cyclobutane-1,3-dicarboxylic acid bis-(2-methoxycarbonyl-tropan-3-yl ester) (490-17-5,113350-55-3,113351-64-7)

Guidance literature:

Multi-step reaction with 2 steps

1: PCl₅

With phosphorus pentachloride;

Reference yield:

α-2,4-diphenylcyclobutane-1,3-dicarboxylic acid dichloride (37597-30-1) + ecgonine (481-37-8) → 2,4-diphenyl-cyclobutane-1,3-dicarboxylic acid bis-(2-methoxycarbonyl-tropan-3-yl ester) (490-17-5,113350-55-3,113351-64-7)

Guidance literature:

α-truxillic acid bis-<2-methoxycarbonyl-tropyl ester>;

upstream raw materials:

α-2,4-diphenylcyclobutane-1,3-dicarboxylic acid dichloride

ecgonine

γ-truxillic anhydride

truxillic acid

Downstream raw materials:

γ-truxillic acid

methylene chloride

truxillic acid

ecgonine