rac-Fluvastatin Methyl Ester (Mixture of diastereoMers)

Base Information

• Chemical Name: rac-Fluvastatin Methyl Ester (Mixture of diastereoMers)
• CAS No.: 202479-37-6
• Molecular Formula: C₂₅H₂₈FNO₄
• Molecular Weight: 425.5
• Mol file: 202479-37-6.mol

Synonyms:

Chemical Property of rac-Fluvastatin Methyl Ester (Mixture of diastereoMers)

Chemical Property:

Purity/Quality:

rac-FluvastatinMethylEster(mixtureofdiastereomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: rac-Fluvastatin Methyl Ester is the racemic analogue of Fluvastatin Methyl Ester (F601275), an intermediate for the selective synthesis of Fluvastatin (F601250).

Technology Process of rac-Fluvastatin Methyl Ester (Mixture of diastereoMers)

There total 9 articles about rac-Fluvastatin Methyl Ester (Mixture of diastereoMers) 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: 84.8%

(E)-7-[3-(4-fluorophenyl)-1-isopropyl-2-indolyl]-3-hydroxy-5-oxo-6-heptenoic acid methyl ester (263274-26-6) → methyl [3R,5S-(E)]-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoate (786710-21-2,202479-37-6)

Guidance literature:

(E)-7-[3-(4-fluorophenyl)-1-isopropyl-2-indolyl]-3-hydroxy-5-oxo-6-heptenoic acid methyl ester; With triethyl borane; oxygen; In tetrahydrofuran; methanol; at -80 - -78 ℃; for 1.03333h;

With sodium tetrahydroborate; In tetrahydrofuran; methanol;

Reference yield: 70.0%

(E)-7-[3-(4-Fluoro-phenyl)-1-isopropyl-1H-indol-2-yl]-5-hydroxy-3-oxo-hept-6-enoic acid methyl ester (93957-52-9) → methyl [3R,5S-(E)]-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoate (786710-21-2,202479-37-6)

Guidance literature:

With methanol; sodium tetrahydroborate; triethyl borane; In tetrahydrofuran; at -70 ℃; for 5h;

DOI:10.1246/cl.1987.1923

Reference yield:

methyl (3S,6E)-7-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]3-hydroxy-5-oxohept-6-enoate → methyl [3R,5S-(E)]-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoate (786710-21-2,202479-37-6)

Guidance literature:

methyl (3S,6E)-7-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]3-hydroxy-5-oxohept-6-enoate; With diethyl methoxy borane; In tetrahydrofuran; methanol; at -78 ℃; for 0.5h;

With sodium tetrahydroborate; In tetrahydrofuran; methanol; for 3h;

With sodium hydrogencarbonate; acetic acid; more than 3 stages;

upstream raw materials:

(E)-7-[3-(4-Fluoro-phenyl)-1-isopropyl-1H-indol-2-yl]-5-hydroxy-3-oxo-hept-6-enoic acid methyl ester

(E)-7-[3-(4-fluorophenyl)-1-isopropyl-2-indolyl]-3-hydroxy-5-oxo-6-heptenoic acid methyl ester

sodium [R*,S*-(E)]-(+/-)-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoate

methyl iodide

Downstream raw materials:

methyl [3R,5S-(E)]-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoate

Refernces

• 1、 -. "Method of separating optically active dihydroxy-heptenoic acid esters". Page/Page column 8; 9; 10; 11. . Retrieved 2008/06/13.
• 2、 -. "PROCESS FOR PREPARATING ENANTIOMERICALLY PURE FLUVASTATIN SODIUM AND A NOVEL POLYMORPHIC FORM THEREOF". Page/Page column 21-22. . Retrieved 2008/06/13.