4579-64-0

Basic information

• Product Name: Methyl 9,10-didehydro-6-methylergoline-8beta-carboxylate
• CAS NO: 4579-64-0
• Molecular Formula: C₁₇H₁₈N₂O₂
• Molecular Weight: 282.342
• Mol File: 4579-64-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Methyl 9,10-didehydro-6-methylergoline-8beta-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 9,10-didehydro-6-methylergoline-8beta-carboxylate(4579-64-0)
• EPA Substance Registry System: Methyl 9,10-didehydro-6-methylergoline-8beta-carboxylate(4579-64-0)

Safety Data

• Hazardous Substances Data: 4579-64-0(Hazardous Substances Data)

Upstream product

• 1449118-00-6 (S,E)-5-(4-bromo-1-tosyl-1H-indol-3-yl)pent-3-en-2-ol 
• 1449117-86-5 (S,E)-4-bromo-3-(4-((tert-butyldimethylsilyl)oxy)pent-2-en-1-yl)-1H-indole 
• 52488-36-5 4-bromo-1H-indole 
• 181271-32-9 4-bromo-1-(4-toluenesulfonyl)indole-3-carboxaldehyde 
• 50-00-0 formaldehyd 
• 87332-72-7 C₁₆H₁₆N₂O₂ 
• 1159774-78-3 (6aR)-4,7-di-tert-butyl 9-methyl 6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-4,7,9-tricarboxylate 
• 1159774-77-2 (6aR,10aS)-4,7-di-tert-butyl 9-methyl 6,6a-dihydroindolo[4,3-fg]quinoline-4,7,9(8H,10aH)-tricarboxylate 
• 1449118-02-8 (6aR,10aS)-di-tert-butyl 9-formyl-6,6a-dihydroindolo[4,3-fg]quinoline-4,7(8H,10aH)-dicarboxylate 
• 1449117-98-9 (6aR,10aS)-di-tert-butyl 9-((S)-1,2-dihydroxyethyl)-6,6a-dihydroindolo[4,3-fg]quinoline-4,7(8H,10aH)-dicarboxylate 
• 1449118-01-7 (6aR,10aS)-di-tert-butyl 9-((S)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecan-5-yl)-6,6a-dihydroindolo[4,3-fg]quinoline-4,7(8H,10aH)-dicarboxylate 
• 1449117-97-8 (6aR,10aS)-di-tert-butyl 9-((S)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecan-5-yl)-6,6a-dihydroindolo[4,3-fg]quinoline-4,7(8H,10aH)-dicarboxylate 
• 1449117-90-1 (2R,5R)-tert-butyl 2-((4-bromo-1-tosyl-1H-indol-3-yl)methyl)-5-((S)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecan-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate 
• 1449117-96-7 tert-butyl ((R)-1-(4-bromo-1-tosyl-1H-indol-3-yl)but-3-en-2-yl)((R)-2-((S)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecan-5-yl)but-3-en-1-yl)carbamate 

Downstream Products

• 916306-98-4 toluene-4-sulfonic acid 2-[(6aR,9R)-7-phenylcarbamoyl-9-(pyrrolidine-1-carbonyl)-6a,7,8,9-tetrahydro-6H-indolo[4,3-fg]quinolin-4-yl]-ethyl ester 
• 916306-95-1 (6aR,9R)-7-phenylcarbamoyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid methyl ester 
• 916306-96-2 (6aR,9R)-7-phenylcarbamoyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid 
• 916306-10-0 (6aR,9R)-9-(pyrrolidine-1-carbonyl)-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-7-carboxylic acid phenylamide 
• 5256-60-0 (+/-)-lysergic acid hydrazide 
• 30334-04-4 6-cyano-9,10-didehydro-ergoline-8-carboxylic acid methyl ester 
• 16727-34-7 (5R,8R)-6-methyl-8β-hydroxymethyl-9α-hydroxyergoline 

Relevant articles and documents

Dimerization of (+)-lysergic acid esters

Dimer isomer mixtures, characterized by a bridgehead C8-C8′ bond, (6a-7a; 6b-7b) were obtained from (+)-lysergic acid methyl or ethyl ester (1b; 1c) in a solution of methanol or ethanol. The isomers were separated, and their structures were determined by detailed NMR measurements and X-ray analysis. Density functional theory was applied to provide insight into the reaction mechanism. Based on an extended examination and the theoretical calculations, a plausible reaction sequence leading to dimers is also presented. The proposed mechanism has been verified by detecting the formation of the superoxide radical anion (O2·-).

Erratum: Total synthesis of lysergic acid (Org. Lett. (2013) 15: 16 (4230-4233) DOI: 10.1021/ol4019562)

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Total synthesis of lysergic acid

A total synthesis of lysergic acid was accomplished. Key features of our synthesis include stereoselective construction of the stereogenic centers at the allylic positions by using the Evans aldol reaction, and a sequential process with a ring-closing metathesis and an intramolecular Heck reaction to construct the C and D rings.