Yohimban-16-carboxylicacid, 17-hydroxy-, methyl ester, (16a,17a)-(?à)-

Base Information

• Chemical Name: Yohimban-16-carboxylicacid, 17-hydroxy-, methyl ester, (16a,17a)-(?à)-
• CAS No.: 24252-70-8
• Molecular Formula: C₂₁H₂₆N₂O₃
• Molecular Weight: 354.449

Synonyms:Yohimban-16a-carboxylic acid, 17a-hydroxy-, methyl ester, (?à)- (8CI); (?à)-Yohimbine

Chemical Property of Yohimban-16-carboxylicacid, 17-hydroxy-, methyl ester, (16a,17a)-(?à)-

Chemical Property:

• Appearance/Colour: light yellow powder
• Melting Point: 234 C
• Water Solubility.: Sparingly soluble
  Purity/Quality:

  99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): UN NO.

MSDS Files:

Useful:

Technology Process of Yohimban-16-carboxylicacid, 17-hydroxy-, methyl ester, (16a,17a)-(?à)-

There total 35 articles about Yohimban-16-carboxylicacid, 17-hydroxy-, methyl ester, (16a,17a)-(?à)- 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: 52.9%

methyl (16α)-17-oxoyohimban-16-carboxylate (2114-90-1,2671-55-8,2671-57-0,18210-73-6,24204-01-1,40088-11-7,41904-77-2,59952-51-1,67711-33-5,83540-87-8,89015-76-9,114030-03-4) → (+/-)-β-yohimbine (84-37-7,131-03-3,146-48-5,483-09-0,483-10-3,522-92-9,522-94-1,549-82-6,549-84-8,2516-78-1,6835-85-4,24252-70-8,25920-66-5,40085-29-8,40085-30-1,40085-32-3,40088-19-5,40088-20-8,40088-25-3,41787-60-4,41904-78-3,59904-75-5,59952-52-2,59952-53-3,59952-56-6,83540-86-7,83540-88-9,103834-06-6,103834-07-7) + 3α-15α-20β-17α-hydroxylyohimbine-16α-carboxylic acid methyl ester (84-37-7,131-03-3,146-48-5,483-09-0,483-10-3,522-92-9,522-94-1,549-82-6,549-84-8,2516-78-1,6835-85-4,24252-70-8,25920-66-5,40085-29-8,40085-30-1,40085-32-3,40088-19-5,40088-20-8,40088-25-3,41787-60-4,41904-78-3,59904-75-5,59952-52-2,59952-53-3,59952-56-6,83540-86-7,83540-88-9,103834-06-6,103834-07-7)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.333333h;

DOI:10.1021/jo00008a025

Reference yield: 52.9%

methyl (16α)-17-oxoyohimban-16-carboxylate (2114-90-1,2671-55-8,2671-57-0,18210-73-6,24204-01-1,40088-11-7,41904-77-2,59952-51-1,67711-33-5,83540-87-8,89015-76-9,114030-03-4) → (+/-)-β-yohimbine (84-37-7,131-03-3,146-48-5,483-09-0,483-10-3,522-92-9,522-94-1,549-82-6,549-84-8,2516-78-1,6835-85-4,24252-70-8,25920-66-5,40085-29-8,40085-30-1,40085-32-3,40088-19-5,40088-20-8,40088-25-3,41787-60-4,41904-78-3,59904-75-5,59952-52-2,59952-53-3,59952-56-6,83540-86-7,83540-88-9,103834-06-6,103834-07-7) + 3α-15α-20β-17α-hydroxylyohimbine-16α-carboxylic acid methyl ester (84-37-7,131-03-3,146-48-5,483-09-0,483-10-3,522-92-9,522-94-1,549-82-6,549-84-8,2516-78-1,6835-85-4,24252-70-8,25920-66-5,40085-29-8,40085-30-1,40085-32-3,40088-19-5,40088-20-8,40088-25-3,41787-60-4,41904-78-3,59904-75-5,59952-52-2,59952-53-3,59952-56-6,83540-86-7,83540-88-9,103834-06-6,103834-07-7)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.333333h;

DOI:10.1021/jo00008a025

Reference yield:

tryptamine (61-54-1) → 3α-15α-20β-17α-hydroxylyohimbine-16α-carboxylic acid methyl ester (84-37-7,131-03-3,146-48-5,483-09-0,483-10-3,522-92-9,522-94-1,549-82-6,549-84-8,2516-78-1,6835-85-4,24252-70-8,25920-66-5,40085-29-8,40085-30-1,40085-32-3,40088-19-5,40088-20-8,40088-25-3,41787-60-4,41904-78-3,59904-75-5,59952-52-2,59952-53-3,59952-56-6,83540-86-7,83540-88-9,103834-06-6,103834-07-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / potassium carbonate / ethanol; H₂O / 0.5 h / Heating

2: 1) m-(chloroperoxy)benzoic acid, 2) triethylamine, acetic anhydride / 1) diethyl ether/dichloromethane, 0 to 20 deg C, 2 h, 2) CH₂Cl₂, 0 deg C, 30 min

3: 95 percent / CH₂Cl₂ / 0.5 h / 20 °C

4: 1) 1,4-diazabicyclo<5.4.0>undec-7-ene (DBU) / 1) N,N-dimethylacetamide, 2) a) 20 deg C, 1h, b) 70 deg C, 1h

5: 50 percent / 50percent aq. sulfuric acid / methanol / 24 h / 20 °C

6: 65.6 percent / conc. hydrochloric acid, H₂ / 10percent Pd-C / methanol / 18 h / 20 °C / 760 Torr

7: 22.2 percent / sodium borohydride / methanol / 0.33 h / 0 °C

With hydrogenchloride; sodium tetrahydroborate; 1,4-diazabicyclo[5.4.0]-7-undecene; sulfuric acid; hydrogen; acetic anhydride; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water;

DOI:10.1021/jo00008a025

upstream raw materials:

methyl (16α)-17-oxoyohimban-16-carboxylate

19,20-didehydroyohimban-17-one

(20β)-18,19-didehydroyohimban-17-one

dimethyl (16α)-17-oxoyohimban-1,16-dicarboxylate

Downstream raw materials:

Yohimbine

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