Isoreserpiline

Base Information

• Chemical Name: Isoreserpiline
• CAS No.: 572-67-8
• Molecular Formula: C23H28N2O5
• Molecular Weight: 412.486
• European Community (EC) Number: 209-342-7
• UNII: 3T56CD574C
• DSSTox Substance ID: DTXSID601317309
• Nikkaji Number: J15.805D
• Wikidata: Q27257999
• Mol file: 572-67-8.mol

Synonyms:Isoreserpiline;572-67-8;Isoreserpilin;iso-reserpiline;3-Isoreserpiline;UNII-3T56CD574C;3T56CD574C;EINECS 209-342-7;methyl (1S,15S,16S,20S)-6,7-dimethoxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate;Methyl (19alpha,20alpha)-16,17-didehydro-10,11-dimethoxy-19-methyloxayohimban-16-carboxylate;Oxayohimban-16-carboxylic acid, 16,17-didehydro-10,11-dimethoxy-19-methyl-, methyl ester, (19.alpha.,20.alpha.)-;NEORESERPILINE;SCHEMBL17088384;DTXSID601317309;3-ISORESERPILINIC ACID, METHYL ESTER;Q27257999;METHYL (19.ALPHA.,20.ALPHA.)-16,17-DIDEHYDRO-10,11-DIMETHOXY-19-METHYLOXAYOHIMBAN-16-CARBOXYLATE;Oxayohimban-16-carboxylic acid, 16,17-didehydro-10,11-dimethoxy-19-methyl-, methyl ester, (19alpha,20alpha)-

Chemical Property of Isoreserpiline

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 412.19982200
• Heavy Atom Count: 30
• Complexity: 699

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CN3CCC4=C(C3CC2C(=CO1)C(=O)OC)NC5=CC(=C(C=C45)OC)OC
• Isomeric SMILES: C[C@H]1[C@@H]2CN3CCC4=C([C@@H]3C[C@@H]2C(=CO1)C(=O)OC)NC5=CC(=C(C=C45)OC)OC

Technology Process of Isoreserpiline

There total 9 articles about Isoreserpiline 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: 2.5%

(1S,4aS,8aS)-7-[2-(5,6-Dimethoxy-1H-indol-3-yl)-ethyl]-1-methyl-7-oxy-4a,5,6,7,8,8a-hexahydro-1H-pyrano[3,4-c]pyridine-4-carboxylic acid methyl ester (81633-50-3,81655-39-2) → (1S,4aS,13cS)-10,11-Dimethoxy-1-methyl-4a,5,6,7,8,13,13b,13c-octahydro-1H-2-oxa-6a,13-diaza-indeno[1,2-c]phenanthrene-4-carboxylic acid methyl ester (81633-51-4) + isoreserpiline (572-67-8) + reserpiline (131-02-2)

Guidance literature:

With trifluoroacetic anhydride; In dichloromethane; at -78 - 5 ℃; for 2h;

Reference yield:

2-Chloro-1-(5,6-dimethoxy-1H-indol-3-yl)ethanone (81633-43-4) → isoreserpiline (572-67-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / NaHCO₃ / dimethylformamide / 3 h / 60 °C

2: 72 percent / NaBH₄, acetic acid / dioxane / 2 h / Heating

3: 1.) Hg(AcO)2, 2.) NaBH₄ / 1.) acetic acid, H₂O, 90 deg C, 1.5 h

With sodium tetrahydroborate; mercury(II) diacetate; sodium hydrogencarbonate; acetic acid; In 1,4-dioxane; N,N-dimethyl-formamide;

Reference yield:

5,6-dimethoxyindole (14430-23-0) → isoreserpiline (572-67-8)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran / -10 °C

2: 4-dimethylaminopyridine, pyridine / tetrahydrofuran / 2 h / Ambient temperature

3: 1.) BH₃*THF, 2.) trimethylamine N-oxide / 1.) THF, RT, 12 h, 2.) MeOH, reflux, 9 h

4: 1.) Hg(AcO)2, 2.) NaBH₄ / 1.) acetic acid, H₂O, 90 deg C, 1.5 h

With pyridine; dmap; sodium tetrahydroborate; borane-THF; trimethylamine-N-oxide; mercury(II) diacetate; In tetrahydrofuran;

upstream raw materials:

2,3-seco-2,3-dihydroreserpiline

(1S,4aS,8aS)-7-[2-(5,6-Dimethoxy-1H-indol-3-yl)-ethyl]-1-methyl-7-oxy-4a,5,6,7,8,8a-hexahydro-1H-pyrano[3,4-c]pyridine-4-carboxylic acid methyl ester

2-Chloro-1-(5,6-dimethoxy-1H-indol-3-yl)ethanone

5,6-dimethoxyindole

Downstream raw materials:

7-(3-bromo-benzoyloxy)-10,11-dimethoxy-19α-methyl-(7ξ,20α)-7H-18-oxa-yohimb-16-ene-16-carboxylic acid methyl ester

Refernces