17β-Hydroxy-19α-methyl-18-oxayohimban-16α-carboxylic acid methyl ester

Base Information

• Chemical Name: 17β-Hydroxy-19α-methyl-18-oxayohimban-16α-carboxylic acid methyl ester
• CAS No.: 55529-55-0
• Molecular Formula: C21H26N2O4
• Molecular Weight: 370.44
• Mol file: 55529-55-0.mol

Synonyms:(7aR,8S,10R,11R,11aS,12aS)-10-Hydroxy-8-methyl-5,6,7a,8,10,11,11a,12,12a,13-decahydro-7H-9-oxa-6a,13-diaza-indeno[2,1-a]anthracene-11-carboxylic acid methyl ester;

Chemical Property of 17β-Hydroxy-19α-methyl-18-oxayohimban-16α-carboxylic acid methyl ester

Chemical Property:

• PSA: 74.79000
• LogP: 2.16740

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: A recently discovered alkaloid, ajmalicinine has been obtained from the root bark of Cabucala striolata. The structure closely resembles that of the preceding base and has been established by chemical and spectroscopic methods.

Technology Process of 17β-Hydroxy-19α-methyl-18-oxayohimban-16α-carboxylic acid methyl ester

There total 13 articles about 17β-Hydroxy-19α-methyl-18-oxayohimban-16α-carboxylic acid methyl ester 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: 48.0%

rac-19-oxo-(15βH)-17-nor-coryn-20-ene-16,16-dicarboxylic acid dimethyl ester (60339-88-0) → (7aS,8S,11S,11aR,12aS)-10-Hydroxy-8-methyl-5,6,7a,8,10,11,11a,12,12a,13-decahydro-7H-9-oxa-6a,13-diaza-indeno[2,1-a]anthracene-11-carboxylic acid methyl ester (20361-93-7,21067-29-8,24196-07-4,55529-55-0,60383-90-6,62058-41-7,63569-17-5,63597-39-7,69349-84-4,81737-76-0,107741-10-6,107741-11-7)

Guidance literature:

With sodium tetrahydroborate; In methanol; acetic acid; for 23h;

Reference yield:

3-Acetyl-1-[2-(1H-indol-3-yl)-ethyl]-pyridinium; bromide (2883-99-0) → (7aS,8S,11S,11aR,12aS)-10-Hydroxy-8-methyl-5,6,7a,8,10,11,11a,12,12a,13-decahydro-7H-9-oxa-6a,13-diaza-indeno[2,1-a]anthracene-11-carboxylic acid methyl ester (20361-93-7,21067-29-8,24196-07-4,55529-55-0,60383-90-6,62058-41-7,63569-17-5,63597-39-7,69349-84-4,81737-76-0,107741-10-6,107741-11-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / NaH / tetrahydrofuran; 1,2-dimethoxy-ethane / 1.) from -15 deg C to RT 3-5 h, 2.) RT, 20 h

2: 48 percent / NaBH₄ / acetic acid; methanol / 23 h

With sodium tetrahydroborate; sodium hydride; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; acetic acid;

Reference yield:

3-Acetyl-1-[2-(1H-indol-3-yl)-ethyl]-pyridinium; bromide (2883-99-0) → (7aS,8S,10R,11S,11aR,12aS)-10-Hydroxy-8-methyl-5,6,7a,8,10,11,11a,12,12a,13-decahydro-7H-9-oxa-6a,13-diaza-indeno[2,1-a]anthracene-11-carboxylic acid methyl ester (20361-93-7,21067-29-8,24196-07-4,55529-55-0,60383-90-6,62058-41-7,63569-17-5,63597-39-7,69349-84-4,81737-76-0,107741-10-6,107741-11-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) THF, DME, -15 deg C, 2) cyclization

2: NaBH₄ / 1) abs.AcOH 2) methanol

With sodium tetrahydroborate;

DOI:10.1016/S0040-4039(00)84444-5

upstream raw materials:

rac-19-oxo-(15βH)-17-nor-coryn-20-ene-16,16-dicarboxylic acid dimethyl ester

3-Acetyl-1-[2-(1H-indol-3-yl)-ethyl]-pyridinium; bromide

ajmalicine

Downstream raw materials:

tetrahydroalstonine

DL-Akuammigin