Methyl 18-hydroxy-11,17-dimethoxyyohimban-16-carboxylate

Base Information

• Chemical Name: Methyl 18-hydroxy-11,17-dimethoxyyohimban-16-carboxylate
• CAS No.: 2901-66-8
• Molecular Formula: C23H30 N2 O5
• Molecular Weight: 414.502
• NSC Number: 81464
• DSSTox Substance ID: DTXSID60951620
• ChEMBL ID: CHEMBL1712538
• Mol file: 2901-66-8.mol

Synonyms:Methyl 18-hydroxy-11,17-dimethoxyyohimban-16-carboxylate;MLS002694431;methyl 17-hydroxy-6,18-dimethoxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;Reserpic acid, methyl ester;NSC-81464;CHEMBL1712538;SCHEMBL15416039;ACon1_002263;DTXSID60951620;MDJQWFFIUHUJSB-UHFFFAOYSA-N;NSC81464;SMR001560360;FT-0674349;Methyl 18-hydroxy-11,17-dimethoxyyohimban-16-carboxylate #;3.beta., 18.beta.-hydroxy-11,17.alpha.-dimethoxy-, methyl ester

Chemical Property of Methyl 18-hydroxy-11,17-dimethoxyyohimban-16-carboxylate

Chemical Property:

• Vapor Pressure: 1.17E-14mmHg at 25°C
• Melting Point: 244.5°C
• Refractive Index: 1.6300 (estimate)
• Boiling Point: 587.8°C at 760 mmHg
• PKA: 14.03±0.60(Predicted)
• Flash Point: 309.3°C
• PSA: 84.02000
• Density: 1.32g/cm³
• LogP: 2.21850
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Dichloromethane, Dimethyl Sulfoxide, Methanol (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 414.21547206
• Heavy Atom Count: 30
• Complexity: 647

Purity/Quality:

ReserpicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(CC2CN3CCC4=C(C3CC2C1C(=O)OC)NC5=C4C=CC(=C5)OC)O

Technology Process of Methyl 18-hydroxy-11,17-dimethoxyyohimban-16-carboxylate

There total 49 articles about Methyl 18-hydroxy-11,17-dimethoxyyohimban-16-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: 97.0%

reserpine (50-55-5) → methyl reserpate (2901-66-8)

Guidance literature:

With methanol; sodium methylate; for 4h; Reflux;

Reference yield:

(3R,4aS,5S,6R,7R,8aS)-3-Cyano-7-hydroxy-6-methoxy-2-[2-(6-methoxy-1H-indol-3-yl)-ethyl]-decahydro-isoquinoline-5-carboxylic acid methyl ester → methyl reserpate (2901-66-8)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 30h;

DOI:10.1021/ja055744x

Reference yield:

(1S,2R,3S,4S,7S)-7-Benzyloxymethyl-3-(fluoro-dimethyl-silanyl)-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester → methyl reserpate (2901-66-8)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂ / Pd/C / ethyl acetate / 30 h / 760 Torr

2: pyridine; 4-dimethylaminopyridine / CH₂Cl₂ / 10 h / Heating

3: m-chloroperbenzoic acid; Na₂PO₄ / CH₂Cl₂ / 15 h / 20 °C

4: Ag₂O; CaSO₄ / 20 h

5: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C

6: MgSO₄ / acetonitrile / 1 h

7: aq. HCl / tetrahydrofuran / 30 h / 20 °C

With pyridine; hydrogenchloride; dmap; calcium sulfate; hydrogen; diisobutylaluminium hydride; magnesium sulfate; 3-chloro-benzenecarboperoxoic acid; silver(l) oxide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetonitrile; 6: Strecker reaction;

DOI:10.1021/ja055744x

upstream raw materials:

reserpine

(1S,2R,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

diazomethane

(1S,2R,3S,4S,7S)-3-(Fluoro-dimethyl-silanyl)-7-hydroxymethyl-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

Downstream raw materials:

ent-18α-(2,5-dimethoxy-benzoyloxy)-11,17β-dimethoxy-15β-yohimban-16α-carboxylic acid methyl ester

ent-18α-hippuroyloxy-11,17β-dimethoxy-15β-yohimban-16α-carboxylic acid methyl ester

ent-18α-[(2,5-dimethoxy-phenyl)-acetoxy]-11,17β-dimethoxy-15β-yohimban-16α-carboxylic acid methyl ester

ent-11,17β-dimethoxy-18α-(2-methoxy-3-nitro-benzoyloxy)-15β-yohimban-16α-carboxylic acid methyl ester