84-37-7

Basic information

• Product Name: methyl (3beta,16alpha)-17-hydroxyyohimban-16-carboxylate
• Synonyms: Methyl (3beta,16alpha)-17-hydroxyyohimban-16-carboxylate; Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (3beta,16alpha)-
• CAS NO: 84-37-7
• Molecular Formula: C₂₁H₂₆N₂O₃
• Molecular Weight: 354.4427
• Mol File: 84-37-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 293° (corr, Maquenne block); mp 268° (open capillary); mp 252-256° (van Tamelen)
• Boiling Point: 543°C at 760 mmHg
• Flash Point: 282.2°C
• Density: 1.31g/cm³
• Vapor Pressure: 1.27E-12mmHg at 25°C
• Refractive Index: 1.66
• CAS DataBase Reference: methyl (3beta,16alpha)-17-hydroxyyohimban-16-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (3beta,16alpha)-17-hydroxyyohimban-16-carboxylate(84-37-7)
• EPA Substance Registry System: methyl (3beta,16alpha)-17-hydroxyyohimban-16-carboxylate(84-37-7)

Safety Data

• Hazardous Substances Data: 84-37-7(Hazardous Substances Data)

Upstream product

• 1218-41-3 1-<2-(1H-indol-3-yl)ethyl>-4-piperidinone 
• 61-54-1 tryptamine 
• 36069-26-8 methyl (20α)-15,16-didehydro-17-oxoyohimban-16-carboxylate 
• 36069-26-8 methyl (20β)-15,16-didehydro-17-oxoyohimban-16-carboxylate 
• 132672-67-4 2,3-dihydro-1-<2-(1H-indol-3-yl)ethyl>-4-methoxypyridinium trifluoromethanesulfonate 
• 132672-75-4 methyl 1,2,6,7,8,8a-hexahydro-2-<2-(1H-indol-3-yl)ethyl>-6-oxo-5-isoquinolinecarboxylate 
• 37734-07-9 methyl endo/exo-3-(bicyclo<2,2,1>hept-5-en-2-yl)-3-oxopropanoate 
• 92579-46-9 2,3-dihydro-1-<2-(1H-indol-3-yl)ethyl>-4(1H)-pyridinone 
• 26822-37-7 N,N-dimethyl-4-oxopiperidinium iodide 
• 37734-05-7 Methyl 3-oxo-4-pentenoate 
• 2114-90-1 methyl (16α)-17-oxoyohimban-16-carboxylate 
• 88966-92-1 dimethyl (16α)-17-oxoyohimban-1,16-dicarboxylate 
• 54725-64-3 (20β)-18,19-didehydroyohimban-17-one 
• 81750-86-9 19,20-didehydroyohimban-17-one 

Downstream Products

• 146-48-5 Yohimbine 

Relevant articles and documents

Total Syntheses of Yohimbe Alkaloids, with Stereoselection for the Normal, Allo, and 3-Epiallo Series, Based on Annelations of 4-Methoxy-1,2-dihydropyridones

N--2,3-dihydro-4-pyridone (31) was generated in two steps (77percent yield) from tryptamine and N-methyl-4-piperidone methiodide.Its cyclization (90percent yield) and oxidation (91percent yield) provided the tetracyclic analogue 32.O-Methylation and Robinson-type annelation of these vinylogous lactams (the latter in form of its Na-carbamate) furnished the dienones 38 (64percent) and 43 (90percent).Further elaboration by cyclization and/or reduction reactions selectively provided the 15,16-didehydroyohimbinones 7 and 44.Their reductions then led to yohimbinone (52, 20percent overall yield from tryptamine), alloyohimbinone (11, 19percent overall yield), and 3-epi-alloyohimbinone (10, 23percent overall yield), which led to yohimbine (3), β-yohimbine (9), 3-epi-alloyohimbine (53), and 3-epi-17-epi-alloyohimbine (54).

Total synthesis of yohimbine.

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