tert-Butyl (E)-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoate

Base Information

• Chemical Name: tert-Butyl (E)-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoate
• CAS No.: 194934-95-7
• Molecular Formula: C₂₈H₃₂FNO₄
• Molecular Weight: 465.565
• Mol file: 194934-95-7.mol

Synonyms:6-Heptenoicacid, 7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-,1,1-dimethylethyl ester, [S-(E)]-;tert-Butyl (E)-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoate;

Chemical Property of tert-Butyl (E)-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoate

Chemical Property:

• Vapor Pressure: 1.16E-17mmHg at 25°C
• Refractive Index: 1.552
• Boiling Point: 647.7 °C at 760 mmHg
• Flash Point: 345.5 °C
• PSA: 68.53000
• Density: 1.13 g/cm³
• LogP: 6.09340
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

O-tert-Butyl-3-ketoFluvastatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: O-tert-Butyl-3-keto Fluvastatin is a reactant in the synthesis of Fluvastatin Sodium Salt (F601250), a synthetic HMG-CoA reductase inhibitor. Antilipemic.

Technology Process of tert-Butyl (E)-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoate

There total 1 articles about tert-Butyl (E)-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoate 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:

acetic acid tert-butyl ester (540-88-5) + (S)-2-acetoxy-1,1,2-triphenylethanol (95061-51-1) + 3-<3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl>-2(E)-propenal (93957-50-7) → (S)-1,1,2-triphenyl-1,2-ethanediol (108998-83-0) + ((S)-(E))-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoic acid 1,1-dimethylethyl ester (194934-95-7)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1016/S0040-4020(97)00686-8

Reference yield:

((S)-(E))-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoic acid 1,1-dimethylethyl ester (194934-95-7) → (S-(R*R*)-(E))-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoic acid 1,1-dimethylethyl ester (194935-00-7,129332-29-2)

Guidance literature:

With acetic acid; tetramethylammonium triacetoxyborohydride; In acetonitrile; at -10 ℃; for 2h;

DOI:10.1016/S0040-4020(97)00686-8

Reference yield:

((S)-(E))-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoic acid 1,1-dimethylethyl ester (194934-95-7) → -7-<3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl>-3,5-dihydroxy-6-heptenoic acid, sodium salt

Guidance literature:

Multi-step reaction with 2 steps

1: tetramethylammonium triacetoxyborohydride, acetic acid / acetonitrile / 2 h / -10 °C

2: aq. NaOH / ethanol / 1.58 h / 25 °C

With sodium hydroxide; acetic acid; tetramethylammonium triacetoxyborohydride; In ethanol; acetonitrile;

DOI:10.1016/S0040-4020(97)00686-8

upstream raw materials:

acetic acid tert-butyl ester

(S)-2-acetoxy-1,1,2-triphenylethanol

3-<3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl>-2(E)-propenal

Downstream raw materials:

(S-(R*R*)-(E))-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoic acid 1,1-dimethylethyl ester

(E)-(3R,5S)-(+)-7-[3-(4-fluoro-phenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxy-hept-6-enoic acid 1,1-dimethylethyl ester

fluvastatin sodium

S-((R*S*)-(E))-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoic acid 1,1-dimethylethyl ester

Refernces