Eserethole

Base Information

• Chemical Name: Eserethole
• CAS No.: 469-23-8
• Molecular Formula: C15H22 N2 O
• Molecular Weight: 246.352
• UNII: IP09BY41GA
• DSSTox Substance ID: DTXSID701135279
• Nikkaji Number: J700.030H
• Mol file: 469-23-8.mol

Synonyms:Eserethole;Eserethol;469-23-8;(-)-Eserethole;IP09BY41GA;(3aR,8bS)-7-ethoxy-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indole;Pyrrolo(2,3-b)indole, 5-ethoxy-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, (3aS,8aR)-;UNII-IP09BY41GA;SCHEMBL8827788;KQWOEHQIZVGMMT-CABCVRRESA-N;DTXSID701135279;(3aS,8aR)-5-Ethoxy-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole;(3aS-cis)-5-ethoxy-1,2,3,3a,8,8a-hexahydro-1,3a, 8-trimethylpyrrolo[2,3-b]indole;(3aS-cis)-5-ethoxy-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo[2,3-b]indole;(3aS-cis)-5-ethoxy-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole

Chemical Property of Eserethole

Chemical Property:

• PSA: 15.71000
• LogP: 2.45730
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Sparingly), Ethanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 246.173213330
• Heavy Atom Count: 18
• Complexity: 322

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=CC2=C(C=C1)N(C3C2(CCN3C)C)C
• Isomeric SMILES: CCOC1=CC2=C(C=C1)N([C@@H]3[C@]2(CCN3C)C)C
• Uses: Eserethol is used in preparation of bisnorcymerine and its acid salt.

Technology Process of Eserethole

There total 11 articles about Eserethole 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: 50.0%

(3S)-5-ethoxy-3-(2-ethoxycarbonylaminoethyl)-1,3-dimethyl-2-oxindole (133343-19-8) → (3AS-cis)-5-ethoxy-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo[2,3-b]indole (469-23-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran;

Reference yield:

(S)-5-ethoxy-1,3-dimethyl-3-(2-methylamino-ethyl)-indolin-2-one → (3AS-cis)-5-ethoxy-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo[2,3-b]indole (469-23-8)

Guidance literature:

With ethanol; sodium;

DOI:10.1021/ja01307a051

Reference yield:

(+/-)-5-ethoxy-1,3-dimethyl-3-(2-methylamino-ethyl)-indolin-2-one (408508-71-4) → (3AS-cis)-5-ethoxy-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo[2,3-b]indole (469-23-8)

Guidance literature:

Multi-step reaction with 2 steps

1: (1S)-2-oxo-bornane-10-sulfonic acid; L_g-tartaric acid

2: sodium; ethanol

With ethanol; L-Tartaric acid; camphor-10-sulfonic acid; sodium;

DOI:10.1021/ja01307a051

upstream raw materials:

d,l-eserethole

(3S)-5-ethoxy-3-(2-ethoxycarbonylaminoethyl)-1,3-dimethyl-2-oxindole

ethanol

(3S)-3-(3-methoxypropyl)-7-methoxy-1,3-dimethyl-5-methylenehexahydro-2-oxindole

Downstream raw materials:

eseroline

(3aS,cis)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-yl-3,4-dihydro-2(1H)-isoquinolinecarboxylate