DL-Eburnamonine

Base Information

• Chemical Name: DL-Eburnamonine
• CAS No.: 2580-88-3
• Molecular Formula: C19H22 N2 O
• Molecular Weight: 294.396
• Mol file: 2580-88-3.mol

Synonyms:Eburnamenin-14(15H)-one,(?à)- (9CI); Vincanorine (7CI);1H-Indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine, eburnamenin-14(15H)-onederiv.; (?à)-Eburnamonine; (?à)-Vincamone; dl-Eburnamonine

Chemical Property of DL-Eburnamonine

Chemical Property:

• Melting Point: 201-202.5°
• PSA: 25.24000
• LogP: 3.71250

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: An optically inactive alkaloid from Vinca minor, the base forms colourless cf'jstals from MeOH or EtOH. It may be characterized as the perchlorate, m.p. 243-5°C and is identical with (±)-Eburnamonine.

Technology Process of DL-Eburnamonine

There total 56 articles about DL-Eburnamonine 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: 85.0%

(+) eburnamenine (517-30-6) → (-)-eburnamonine (2580-88-3,4880-88-0,53494-54-5,60384-17-0,71697-48-8,474-00-0)

Guidance literature:

(+) eburnamenine; With hydrogenchloride; In water; at 20 ℃; for 4h; Inert atmosphere;

With pyridinium dichromate; In dichloromethane; water; for 0.5h; Inert atmosphere;

DOI:10.1016/j.chempr.2017.04.007

Reference yield: 84.0%

3-((1R,12bR)-1-Ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-1-yl)-2-[(E)-hydroxyimino]-propionic acid methyl ester (86708-31-8) → (-)-eburnamonine (2580-88-3,4880-88-0,53494-54-5,60384-17-0,71697-48-8,474-00-0)

Guidance literature:

With sodium hydroxide; In water; ethylene glycol; at 155 - 160 ℃; for 3h;

Reference yield: 62.0%

C20H25N2O2(1+)*ClO4(1-) → (-)-eburnamonine (2580-88-3,4880-88-0,53494-54-5,60384-17-0,71697-48-8,474-00-0) + (–)-20-epi-eburnamonine (71697-48-8)

Guidance literature:

C₂₀H₂₅N₂O₂⁽¹⁺⁾*ClO₄^(1-); With palladium 10% on activated carbon; hydrogen; In N,N-dimethyl-formamide; at 23 ℃; for 3.5h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 23 ℃; for 3h;

DOI:10.1002/anie.202106184

upstream raw materials:

14,15-dihydroeburnamenin-14-ol

3-((1R,12bR)-1-Ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-1-yl)-2-[(E)-hydroxyimino]-propionic acid methyl ester

ent-19-oxo-eburnamonine

(+/-)-Eburnamonine lactam

Downstream raw materials:

14,15-dihydroeburnamenin-14-ol

Refernces

• 1、 Hayashida, Kohei,Korch, Katerina M.,Ngamnithiporn, Aurapat,Reimann, Christopher E.,Saito, Daisuke,Stoltz, Brian M.. "The Enantioselective Synthesis of Eburnamonine, Eucophylline, and 16′-epi-Leucophyllidine". . p. 17957 - 17962. Retrieved 2021/07/12.
• 2、 Nidhiry, John Eugene,Prasad, Kavirayani R.. "Enantiospecific total synthesis of indole alkaloids (+)-eburnamonine, (-)-aspidospermidine and (-)-quebrachamine". . p. 5525 - 5536. Retrieved 2013/07/05.