(+)-Eseroline

Base Information

• Chemical Name: (+)-Eseroline
• CAS No.: 29347-15-7
• Molecular Formula: C₁₃H₁₈N₂O
• Molecular Weight: 218.299
• UNII: 66D41T0962
• Nikkaji Number: J1.556.719H
• Wikidata: Q27263994
• ChEMBL ID: CHEMBL73782
• Mol file: 29347-15-7.mol

Synonyms:eseroline;eseroline monohydrochloride, (3aS-cis)-isomer;eseroline, (+)-;eseroline, (3aR-cis)-isomer

Chemical Property of (+)-Eseroline

Chemical Property:

• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 218.141913202
• Heavy Atom Count: 16
• Complexity: 296

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC12CCN(C1N(C3=C2C=C(C=C3)O)C)C
• Isomeric SMILES: C[C@]12CCN([C@H]1N(C3=C2C=C(C=C3)O)C)C

Technology Process of (+)-Eseroline

There total 15 articles about (+)-Eseroline 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: 97.6%

physostigmine (29347-10-2) → (+)-Eseroline (29347-15-7,70354-71-1,469-22-7)

Guidance literature:

With sodium hydroxide; In ethanol; for 4h; Ambient temperature;

DOI:10.1021/jm00379a020

Reference yield:

(3aR,8aS)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole (104069-12-7) → (+)-Eseroline (29347-15-7,70354-71-1,469-22-7)

Guidance literature:

With boron tribromide; In dichloromethane; for 2h; Yield given; Ambient temperature;

Reference yield:

(Z)-2-Methyl-4-triisopropylsilanyloxy-but-2-enoic acid (153109-50-3) → (+)-Eseroline (29347-15-7,70354-71-1,469-22-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 55 percent / DCC, HOBT / tetrahydrofuran / Heating

2: Pd₂(dba)3*CHCl₃, (R)-BINAP, 1,2,2,6,6-pentamethylpiperidine / N,N-dimethyl-acetamide / 1.5 h / 100 °C

3: 3M aq. HCl / tetrahydrofuran / Ambient temperature

4: 1.) Et₃N, MgSO₄, 2.) LiAlH₄ / 1.) THF, RT, overnight, 2.) THF, reflux, 1.5 h

5: BBr₃ / CH₂Cl₂ / 23 °C

With 1,2,2,6,6-pentamethylpiperidine; hydrogenchloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; lithium aluminium tetrahydride; boron tribromide; magnesium sulfate; benzotriazol-1-ol; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide;

DOI:10.1021/ja980788+

upstream raw materials:

(3aR,8aS)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole

physostigmine

2-iodo-4-methoxy-N-methylaniline

(Z)-2-Methyl-4-triisopropylsilanyloxy-but-2-enoic acid

Downstream raw materials:

physostigmine

O-(chloroethyl)eseroline

(+)-physostigmine salicylate

(+)-(3aR)-3a,8-dimethyl-2,3,3a,8a-tetrahydrofuro[2,3-b]indol-5-ol