38940-64-6

Basic information

• Product Name: 5-(1-Hydroxyethyl)-3-pyridinecarboxylic acid methyl ester
• Synonyms: 5-(1-Hydroxyethyl)-3-pyridinecarboxylic acid methyl ester
• CAS NO: 38940-64-6
• Molecular Formula: C₉H₁₁NO₃
• Molecular Weight: 0
• Mol File: 38940-64-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-(1-Hydroxyethyl)-3-pyridinecarboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(1-Hydroxyethyl)-3-pyridinecarboxylic acid methyl ester(38940-64-6)
• EPA Substance Registry System: 5-(1-Hydroxyethyl)-3-pyridinecarboxylic acid methyl ester(38940-64-6)

Safety Data

• Hazardous Substances Data: 38940-64-6(Hazardous Substances Data)

Upstream product

• 182483-71-2 5-(1-Bromo-ethyl)-nicotinic acid methyl ester 
• 668987-16-4 methyl 5-acetyl-4-[(β-carbolin-1-yl)methyl]-1,4-dihydropyridine-3-carboxylate 
• 38940-61-3 methyl 5-acetylpyridine-3-carboxylate 
• 668987-10-8 methyl 1,5-diacetyl-4-[(β-carbolin-1-yl)methyl]-1,4-dihydropyridine-3-carboxylate 
• 68686-58-8 methyl 5-ethylpyridine-3-carboxylate 
• 182483-52-9 2-Cyano-hex-2-enoic acid methyl ester 
• 152362-06-6 methyl 2-chloro-5-ethyl-3-pyridinecarboxylate 
• 64-17-5 ethanol 

Relevant articles and documents

Total syntheses of tacamide-type indole alkaloids of Tabernaemontana eglandulosa

Total syntheses are described for seven tacamine-type indole alkaloids (1-7) found in Tabernaemontana eglandulosa. (±)-Tacamine (1), (±)-16-epitacamine (2), and (±)-apotacamine (3) were prepared from pentacyclic intermediates 18. Apotacamine (3) was also obtained from aldehyde 12 via epimerization of 20-epiapotacamine (19) by the Polonovski-Potier reaction. Homologation of ester 13 led to 20-epitacamonine (23), which was similarly converted to (±)-tacamonine (4). Reduction of 4 gave (±)-descarbomethoxytacamines 5 and 6. Aldehyde 11 was reacted with trimethylsilyl cyanide (TMSCN) to yield the two (±)-17-hydroxytacamonines (7), of which the isomer with an axial hydroxy group (17β-OH) was found to be identical with the natural compound. Finally, an attempt to prepare (±)-19S-hydroxytacamine (8) is described. As an intermediate for this, a new synthesis of the pyridine alkaloid methyl 5-(1'-hydroxyethyl)nicotinate (34) was achieved.

Total Synthesis of the Proposed Structures of Indole Alkaloids Lyaline and Lyadine

The harman-1,4-dihydropyridines 1 and 2, which constitute the originally proposed structures for the indole alkaloids lyaline and lyadine, have been synthesized, and their NMR data have been compared with those available for the natural products. Due to the discrepancies in the spectral data, the structures of lyadine and lyaline should be revised.