(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester

Base Information

• Chemical Name: (4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester
• CAS No.: 147489-06-3
• Molecular Formula: C32H36FNO4
• Molecular Weight: 517.641
• Hs Code.: 2934999090
• Mol file: 147489-06-3.mol

Synonyms:1,3-Dioxane-4-aceticacid,6-[2-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-,1,1-dimethylethyl ester, [4R-[4a,6a(E)]]-;(3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-2,2-Dimethyl-1,3-dioxane-6-heptenoic acid,1,1-dimethylethyl ester;

Chemical Property of (4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester

Chemical Property:

• Appearance/Colour: white or almost white power
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 105-116 °C(Solv: hexane (110-54-3))
• Refractive Index: 1.604
• Boiling Point: 604.559 °C at 760 mmHg
• PKA: 4.61±0.50(Predicted)
• Flash Point: 319.426 °C
• PSA: 57.65000
• Density: 1.184 g/cm³
• LogP: 7.57350
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

≥98.0% ^*data from raw suppliers

t-Butyl(3R,5S)-7-[2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-isopropylidenedioxy-6-heptenoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: t-Butyl (3R,5S)-7-[2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-isopropylidenedioxy-6-heptenoate is an impurity from the synthesis of HMG-CoA reductase inhibitor Pitavastatin [P531040, (Z)-Pitavastatin Calcium Salt].

Technology Process of (4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester

There total 51 articles about (4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester 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: 89.6%

C21H28N2O6S2 + 2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline (121660-37-5) → (4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester (147489-06-3)

Guidance literature:

With sodium t-butanolate; In tetrahydrofuran; at -10 - 25 ℃; for 4h;

Reference yield: 89.3%

C15H24N2O6S2 + 2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline (121660-37-5) → (4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester (147489-06-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 25 ℃; for 4h;

Reference yield: 89.0%

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate (124752-23-4) + diethyl <2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methylphosphonate (154057-57-5) → (4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester (147489-06-3)

Guidance literature:

With lithium chloride; In tetrahydrofuran; at 0 - 35 ℃; for 5.66667h; Reagent/catalyst; Inert atmosphere;

upstream raw materials:

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

<2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methyl(diphenyl)phosphine oxide

2-cyclopropyl-4-(4-fluorophenyl)-3-iodoquinoline

t-butyl (3R,5S)-3,5-dihydroxy-6-heptynoate

Downstream raw materials:

pitavastatin

sodium (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxyhept-6-enoate

(3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-3,5-dihydroxy-6-heptenoic acid tert-butyl ester

pitavastatin calcium salt

Refernces

• 1、 -. "Synthetic method of pitavastatin tert-butyl ester". Paragraph 0013; 0051; 0055; 0063-0064; 0075-0076. . Retrieved 2020/11/22.
• 2、 -. "Preparation method of statins intermediate". Paragraph 0057-0060; 0067-0070; 0077-0080; 0087-0090. . Retrieved 2018/11/27.