Ajmalan-17,21-diol,1,2,19,20-tetradehydro-1-demethyl-, 17-acetate (9CI)

Base Information

• Chemical Name: Ajmalan-17,21-diol,1,2,19,20-tetradehydro-1-demethyl-, 17-acetate (9CI)
• CAS No.: 107585-43-3
• Molecular Formula: C₂₁H₂₂N₂O₃
• Molecular Weight: 350.417
• Mol file: 107585-43-3.mol

Synonyms:6H-6,10:11,12a-Dimethanoindolo[3,2-b]quinolizine,ajmalan-17,21-diol deriv.; Raucaffriline

Chemical Property of Ajmalan-17,21-diol,1,2,19,20-tetradehydro-1-demethyl-, 17-acetate (9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Ajmalan-17,21-diol,1,2,19,20-tetradehydro-1-demethyl-, 17-acetate (9CI)

There total 20 articles about Ajmalan-17,21-diol,1,2,19,20-tetradehydro-1-demethyl-, 17-acetate (9CI) 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: 75.0%

C24H23Cl3N2O5 (134277-02-4,134277-03-5) → (19Z)-Vomilenine (6880-50-8,107585-43-3,134356-24-4)

Guidance literature:

With acetic acid; zinc; for 1.5h; Ambient temperature;

DOI:10.1248/cpb.39.266

Reference yield: 68.0%

C24H23Cl3N2O5 (134277-02-4,134277-03-5) → Vomilenine (6880-50-8,107585-43-3,134356-24-4)

Guidance literature:

With acetic acid; zinc; for 3h; Ambient temperature;

DOI:10.1248/cpb.39.266

Reference yield:

C22H32N4O (2552-93-4) → Vomilenine (6880-50-8,107585-43-3,134356-24-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 1 N NaOH / CH₂Cl₂ / 0.67 h / Ambient temperature

2: 86 percent / H₂O, CuCl₂ / tetrahydrofuran / 36 h / Ambient temperature; pH 7 (phosphate buffer)

3: 93 percent / pyridine / Ambient temperature

4: 88 percent / lead tetraacetate / CH₂Cl₂ / 1 h / -70 to 0 deg C

5: triethylamine / CH₂Cl₂ / 5 h / Ambient temperature

6: N-bromosuccinimide, triethylamine / CH₂Cl₂ / 0.17 h / 0 °C

7: 26 percent / Li₂CO₃ / dimethylformamide / 4.5 h / 80 °C

8: 68 percent / zinc dust, acetic acid / 3 h / Ambient temperature

With pyridine; lead(IV) acetate; sodium hydroxide; N-Bromosuccinimide; water; lithium carbonate; acetic acid; triethylamine; copper dichloride; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.39.266

upstream raw materials:

C₂₄H₂₃Cl₃N₂O₅

C₂₂H₃₂N₄O

C₂₃H₂₇Cl₃N₂O₄

C₂₄H₂₅Cl₃N₂O₅

Downstream raw materials:

raucaffricine

Perakine

Refernces

• 1、 Takayama,Phisalaphong,Kitajima,Aimi,Sakai,Stockigt. "Partial synthesis of Rauwolfia alkaloids, vomilenine and (19Z)-vomilenine, and their relative thermodynamic stability as revealed by their transformation into perakine". . p. 266 - 269. Retrieved 2007/10/02.