cis-(+-)-1-Ethyl-1,2,3,3a,8,8a-hexahydroindeno(2,1-b)pyrrol-5-yl hexylcarbamate

Base Information

• Chemical Name: cis-(+-)-1-Ethyl-1,2,3,3a,8,8a-hexahydroindeno(2,1-b)pyrrol-5-yl hexylcarbamate
• CAS No.: 139761-06-1
• Molecular Formula: C20H30N2O2
• Molecular Weight: 330.4644
• DSSTox Substance ID: DTXSID60930591
• Nikkaji Number: J482.773B
• Wikidata: Q76278641
• Pharos Ligand ID: P2RDTSCLR9WT
• ChEMBL ID: CHEMBL1085384
• Mol file: 139761-06-1.mol

Synonyms:BRN 5449611;CHEMBL1085384;cis-(+-)-1-Ethyl-1,2,3,3a,8,8a-hexahydroindeno(2,1-b)pyrrol-5-yl hexylcarbamate;139761-06-1;Carbamic acid, hexyl-, 1-ethyl-1,2,3,3a,8,8a-hexahydroindeno(2,1-b)pyrrol-5-yl ester, cis-(+-)-;DTXSID60930591;BDBM50318758;LS-49861;(3aS,8aR)-1-ethyl-1,2,3,3a,8,8a-hexahydroindeno[2,1-b]pyrrol-5-yl hexylcarbamate;1-Ethyl-1,2,3,3a,8,8a-hexahydroindeno[2,1-b]pyrrol-5-yl hydrogen hexylcarbonimidate;1-Ethyl-5-(hexylcarbamoyloxy)-1,2,3,3aalpha,8,8aalpha-hexahydroindeno[2,1-b]pyrrole

Chemical Property of cis-(+-)-1-Ethyl-1,2,3,3a,8,8a-hexahydroindeno(2,1-b)pyrrol-5-yl hexylcarbamate

Chemical Property:

• Vapor Pressure: 1.25E-07mmHg at 25°C
• Boiling Point: 430.9°C at 760 mmHg
• Flash Point: 214.4°C
• Density: 1.064g/cm³
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 330.230728204
• Heavy Atom Count: 24
• Complexity: 414

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCNC(=O)OC1=CC2=C(CC3C2CCN3CC)C=C1
• Isomeric SMILES: CCCCCCNC(=O)OC1=CC2=C(C[C@@H]3[C@H]2CCN3CC)C=C1

Technology Process of cis-(+-)-1-Ethyl-1,2,3,3a,8,8a-hexahydroindeno(2,1-b)pyrrol-5-yl hexylcarbamate

There total 7 articles about cis-(+-)-1-Ethyl-1,2,3,3a,8,8a-hexahydroindeno(2,1-b)pyrrol-5-yl hexylcarbamate 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:

1,3,3a,8a-tetrahydro-5-methoxyindeno<2,1-b>pyrrole-2,8-dione (36285-93-5) → Hexyl-carbamic acid 1-ethyl-1,2,3,3a,8,8a-hexahydro-indeno[2,1-b]pyrrol-5-yl ester (139761-06-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / H₂, HCl(gas) / 10percent Pd/C / acetic acid / 4 h / 70 °C / 2585.7 Torr

2: 96 percent / LiAlH₄ / tetrahydrofuran / 5 h / Heating

3: pyridine / CH₂Cl₂ / 1 h / Ambient temperature

4: 1.) BH₃-Me₂S, 2.) concd. HCl / 1.) THF, reflux, 3 h, 2.) THF, methanol, RT, overnight

5: 48percent aq. HBr / 4 h / Heating

6: NaH / benzene / 2 h / Ambient temperature

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; dimethylsulfide borane complex; hydrogen bromide; hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; acetic acid; benzene;

DOI:10.1021/jm00086a011

Reference yield:

methyl 2,3-dihydro-2-(hydroxyimino)-6-methoxy-3-oxo-1H-indene-1-acetate (36286-07-4) → Hexyl-carbamic acid 1-ethyl-1,2,3,3a,8,8a-hexahydro-indeno[2,1-b]pyrrol-5-yl ester (139761-06-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 72 percent / H₂, HCl(gas) / 10percent Pd/C / acetic acid / 4 h / 2585.7 Torr / Heating

2: 96 percent / H₂, HCl(gas) / 10percent Pd/C / acetic acid / 4 h / 70 °C / 2585.7 Torr

3: 96 percent / LiAlH₄ / tetrahydrofuran / 5 h / Heating

4: pyridine / CH₂Cl₂ / 1 h / Ambient temperature

5: 1.) BH₃-Me₂S, 2.) concd. HCl / 1.) THF, reflux, 3 h, 2.) THF, methanol, RT, overnight

6: 48percent aq. HBr / 4 h / Heating

7: NaH / benzene / 2 h / Ambient temperature

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; dimethylsulfide borane complex; hydrogen bromide; hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; acetic acid; benzene;

DOI:10.1021/jm00086a011

Reference yield:

1,2,3,3a,8,8a-hexahydro-5-methoxyindeno<2,1-b>pyrrole (46271-61-8) → Hexyl-carbamic acid 1-ethyl-1,2,3,3a,8,8a-hexahydro-indeno[2,1-b]pyrrol-5-yl ester (139761-06-1)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / CH₂Cl₂ / 1 h / Ambient temperature

2: 1.) BH₃-Me₂S, 2.) concd. HCl / 1.) THF, reflux, 3 h, 2.) THF, methanol, RT, overnight

3: 48percent aq. HBr / 4 h / Heating

4: NaH / benzene / 2 h / Ambient temperature

With pyridine; hydrogenchloride; dimethylsulfide borane complex; hydrogen bromide; sodium hydride; In dichloromethane; benzene;

DOI:10.1021/jm00086a011

upstream raw materials:

Hexyl isocyanate

1,2,3,3a,8,8a-hexahydro-5-methoxyindeno<2,1-b>pyrrole

3,3a,8,8a-tetrahydro-5-methoxyindeno<2,1-b>pyrrol-2(1H)-one

1,3,3a,8a-tetrahydro-5-methoxyindeno<2,1-b>pyrrole-2,8-dione

Refernces