Eburnamenine-14-methanol, 14,15-dihydro-, (3-alpha)-

Base Information

• Chemical Name: Eburnamenine-14-methanol, 14,15-dihydro-, (3-alpha)-
• CAS No.: 105500-12-7
• Deprecated CAS: 108567-71-1
• Molecular Formula: C20H26 N2 O
• Molecular Weight: 310.4332
• DSSTox Substance ID: DTXSID60147162
• Nikkaji Number: J389.405C
• Mol file: 105500-12-7.mol

Synonyms:RGH 0537;RGH-0537;Eburnamenine-14-methanol, 14,15-dihydro-, (3-alpha)-;105500-12-7;(-)-(3-alpha,14-alpha,16-alpha)-14,15-Dihydroerburnamenine-14-methanol;1H-Indolo(3,2,1-de)pyrido(3,2,1-ij)-1,5-naphthyridine, (-)-(3S,14R,16R)-16-ethyl-14-hydroxymethyl-3,4,5,6,14,15,16,17,18,19-decahydro-;SCHEMBL10569791;DTXSID60147162;(3S)-14,15-Dihydroeburnamenine-14alpha-methanol

Chemical Property of Eburnamenine-14-methanol, 14,15-dihydro-, (3-alpha)-

Chemical Property:

• Vapor Pressure: 1.47E-10mmHg at 25°C
• Boiling Point: 493.6°Cat760mmHg
• Flash Point: 252.3°C
• Density: 1.31g/cm³
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 310.204513457
• Heavy Atom Count: 23
• Complexity: 469

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC12CCCN3C1C4=C(CC3)C5=CC=CC=C5N4C(C2)CO
• Isomeric SMILES: CC[C@]12CCCN3[C@@H]1C4=C(CC3)C5=CC=CC=C5N4[C@H](C2)CO

Technology Process of Eburnamenine-14-methanol, 14,15-dihydro-, (3-alpha)-

There total 8 articles about Eburnamenine-14-methanol, 14,15-dihydro-, (3-alpha)- 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: 84.0%

(3S,16R,14R)-14-deoxyvincamine (105500-11-6) → (-)-3S,16R,14R-14,15-dihydro-14-hydroxymethyl-eburnamenine (105500-12-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 1h;

Reference yield:

(-)-3S,16R-14-hydroxymethyl-eburnamenine (105500-14-9) → (-)-3S,16R,14R-14,15-dihydro-14-hydroxymethyl-eburnamenine (105500-12-7)

Guidance literature:

With ammonia; platinum (IV) oxide; In methanol; ethanol; water; acetic acid;

Reference yield:

methyl (1R,12bS)-1-ethyl-1,2,3,4,6,7,12,12b-octahydro-α-(hydroxyimino)indolo<2,3-a>quinolizine-1-propionate, hydrochloride → (-)-3S,16R,14R-14,15-dihydro-14-hydroxymethyl-eburnamenine (105500-12-7)

Guidance literature:

Multi-step reaction with 5 steps

1: conc. aq. NH₃ / H₂O; CHCl₃

2: 89 percent / p-toluenesulfonic acid monohydrate / toluene / 1.5 h / Heating

3: 89 percent / formic acid / 10percent Pd/C / methanol; dimethylformamide / 1.5 h / 50 °C

4: 80 percent / sodium methoxide / methanol / 2 h / Heating

5: 84 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

With ammonium hydroxide; lithium aluminium tetrahydride; formic acid; sodium methylate; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform; water; N,N-dimethyl-formamide; toluene;

upstream raw materials:

(3S,16R,14R)-14-deoxyvincamine

(3S,16R,14S)-14-deoxyvincamine

14,15-dehydro-16-epivincamine

methyl (1R,12bS)-1-ethyl-1,2,3,4,6,7,12,12b-octahydro-α-(hydroxyimino)indolo<2,3-a>quinolizine-1-propionate

Refernces

• 1、 -. "Eburnamenine derivatives, pharmaceutical compositions and methods employing them and processes for their preparation". . . Retrieved 2008/06/13.