Aliskiren inter-9

Base Information

• Chemical Name: Aliskiren inter-9
• CAS No.: 866030-33-3
• Molecular Formula: C28H46N2O5
• Molecular Weight: 490.684
• Mol file: 866030-33-3.mol

Synonyms:(2S,5R)-3,6-Diethoxy-2,5-dihydro-2-[(2S)-2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-3-methylbutyl]-5-(1-methylethyl)pyrazine;Aliskiren inter-9

Chemical Property of Aliskiren inter-9

Chemical Property:

• Refractive Index: 1.511
• Boiling Point: 562.2 °C at 760 mmHg
• Flash Point: 234.2 °C
• PSA: 70.87000
• Density: 1.06 g/cm³
• LogP: 4.46330

Purity/Quality:

99% ^*data from raw suppliers

(2S,5R)-3,6-Diethoxy-2,5-dihydro-2-[(2S)-2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-3-methylbutyl]-5-(1-methylethyl)pyrazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Aliskiren inter-9

There total 10 articles about Aliskiren inter-9 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: 68.0%

(2R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine (110117-71-0) + (R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene (172900-69-5) → (2R,5S)-3,6-diethoxy-2-isopropyl-5-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-2,5-dihydropyrazine (866030-33-3)

Guidance literature:

With n-butyllithium;

DOI:10.1016/j.tetlet.2005.07.028

Reference yield:

4-methoxy-3-(3-methoxypropoxy)benzaldehyde (172900-75-3) → (2R,5S)-3,6-diethoxy-2-isopropyl-5-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-2,5-dihydropyrazine (866030-33-3)

Guidance literature:

Multi-step reaction with 7 steps

1: NaBH₄ / ethanol

2: PBr₃ / CH₂Cl₂

3: 76 percent / LiHMDS / tetrahydrofuran

4: 81 percent / LiOH; H₂O₂

5: 95 percent / LAH / tetrahydrofuran

6: 97 percent / PPh₃; NBS / CH₂Cl₂

7: 68 percent / n-BuLi

With lithium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; dihydrogen peroxide; phosphorus tribromide; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/j.tetlet.2005.07.028

Reference yield:

(R)-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-(1-methylethyl)propanoic acid (172900-71-9) → (2R,5S)-3,6-diethoxy-2-isopropyl-5-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-2,5-dihydropyrazine (866030-33-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / LAH / tetrahydrofuran

2: 97 percent / PPh₃; NBS / CH₂Cl₂

3: 68 percent / n-BuLi

With N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2005.07.028

upstream raw materials:

(2R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

isovanillin

(R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one

Downstream raw materials:

ethyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate

(2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexan-1-ol

(2S,4S,5S,7S)-5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

Benzyl-((1S,2R,4S)-4-benzyloxymethyl-2-hydroxy-1-{(S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyl}-5-methyl-hexyl)-carbamic acid tert-butyl ester