Name | Intermediate of Eletriptan |
Synonyms | Intermediate of Eletriptan (R)-5-bromo-3-[(1-methyl-2-pyrrolidinyl)methyl]-1H-indole Benzyl (2R)-2-[(5-bromo-1H-indol-3-yl)carbonyl]pyrrolidine-1-carboxylate (R)-2-[(5-Bromo-1H-indol-3-yl)carbonyl]-1-pyrrolidinecarboxylic acid benzyl ester 1-pyrrolidinecarboxylic acid, 2-[(5-bromo-1H-indol-3-yl)carbonyl]-, phenylmethyl ester, (2R)- |
CAS | 143322-56-9 |
InChI | InChI=1/C21H19BrN2O3/c22-15-8-9-18-16(11-15)17(12-23-18)20(25)19-7-4-10-24(19)21(26)27-13-14-5-2-1-3-6-14/h1-3,5-6,8-9,11-12,19,23H,4,7,10,13H2/t19-/m1/s1 |
Molecular Formula | C14H17BrN2 |
Molar Mass | 427.291 |
Density | 1.505g/cm3 |
Boling Point | 605°C at 760 mmHg |
Flash Point | 319.7°C |
Vapor Presure | 1.38E-14mmHg at 25°C |
pKa | 14.40±0.30(Predicted) |
Storage Condition | 2-8°C |
Refractive Index | 1.678 |
Use | Intermediate |
1mg | 5mg | 10mg | |
---|---|---|---|
1 mM | 2.34 ml | 11.702 ml | 23.403 ml |
5 mM | 0.468 ml | 2.34 ml | 4.681 ml |
10 mM | 0.234 ml | 1.17 ml | 2.34 ml |
5 mM | 0.047 ml | 0.234 ml | 0.468 ml |
The preparation method of the irittretan intermediate (R)-3-(N-benzyloxycarbonylpyrrolidin-2-ylcarbonyl)-5-bromo-1H-indole published at home and abroad is only reported above, This method uses Grignard reagent-ethylmagnesium bromide as a condensing agent, and there are many shortcomings: Grignard reagent is unstable in nature; high requirements for preparation and operating conditions, and there are; the content of the finished products sold in the market is unstable, the quality is poor and the cost is more expensive, the reaction region selectivity is poor, and more 1-bit substitution by-products are generated, resulting in low yield and purity, so it is not suitable for large-scale industrial production.