methyl (6aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

Base Information

• Chemical Name: methyl (6aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate
• CAS No.: 30341-92-5
• Molecular Formula: C16H18 N2 O2
• Molecular Weight: 270.331
• European Community (EC) Number: 805-980-0
• Mol file: 30341-92-5.mol

Synonyms:SCHEMBL7682132;30341-92-5

Chemical Property of methyl (6aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

Chemical Property:

• Vapor Pressure: 5.33E-09mmHg at 25°C
• Boiling Point: 469.8°Cat760mmHg
• PKA: 17.40±0.40(Predicted)
• Flash Point: 237.9°C
• PSA: 54.12000
• Density: 1.248g/cm³
• LogP: 2.28750
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 270.136827821
• Heavy Atom Count: 20
• Complexity: 400

Purity/Quality:

99%, ^*data from raw suppliers

ERGOLINE-8-CARBOXYLIC ACID METHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CC2C(CC3=CNC4=CC=CC2=C34)NC1
• Isomeric SMILES: COC(=O)C1CC2[C@@H](CC3=CNC4=CC=CC2=C34)NC1

Technology Process of methyl (6aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

There total 20 articles about methyl (6aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-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: 72.0%

9-methyl 7-(2,2,2-trichloroethyl) (6aR,9R,10aR)-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-7,9(4H)-dicarboxylate (80993-64-2) → methyl (6aR,9R,10aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate (30341-92-5)

Guidance literature:

With acetic acid; zinc; for 60h; Heating;

DOI:10.1002/jps.2600701207

Reference yield:

D-6-cyano-8β-methoxycarbonylergoline (51260-62-9) → methyl (6aR,9R,10aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate (30341-92-5)

Guidance literature:

With hydrogen; W-7 Raney Ni; In N,N-dimethyl-formamide;

DOI:10.1248/cpb.42.1463

Reference yield:

9,10-dihydrolysergic acid methyl ester (3006-19-7,5143-94-2,35470-53-2,77842-02-5,87247-99-2,96648-31-6,96648-32-7) → methyl (6aR,9R,10aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate (30341-92-5)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂

2: H₂ / W-7 Raney Ni / dimethylformamide

With hydrogen; W-7 Raney Ni; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.42.1463

upstream raw materials:

methanol

4,5-dihydro-indolo[4,3-fg]quinoline-9-carboxylic acid ethyl ester

4-acetyl-4,5-dihydro-indolo[4,3-fg]quinoline-9-carbonitrile

9-methyl 7-(2,2,2-trichloroethyl) (6aR,9R,10aR)-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-7,9(4H)-dicarboxylate

Downstream raw materials:

rac-6-methyl-5α-ergoline-8β-carboxylic acid methyl ester

rac-6-methyl-5α-ergoline-8α-carboxylic acid methyl ester

rac-6-ethyl-ergoline-8β-carboxylic acid methyl ester

rac-6-propyl-ergoline-8β-carboxylic acid methyl ester

Refernces

• 1、 Stoll,Petrzilka. "-". . p. 1137,1141. Retrieved 1953.
• 2、 Troxler, Thomas,Enz, Albert,Hoyer, Daniel,Langenegger, Daniel,Neumann, Peter,Pfaeffli, Paul,Schoeffter, Philippe,Hurth, Konstanze. "Ergoline derivatives as highly potent and selective antagonists at the somatostatin sst1 receptor". . p. 979 - 982. Retrieved 2008/09/18.