(1'S,3S)-1-(1'-naphthyl)ethyl methyl 3-(4-bromophenyl)pentanedioate

Base Information

• Chemical Name: (1'S,3S)-1-(1'-naphthyl)ethyl methyl 3-(4-bromophenyl)pentanedioate
• CAS No.: 1315282-24-6
• Molecular Formula: C₂₄H₂₃BrO₄
• Molecular Weight: 455.348
• Mol file: 1315282-24-6.mol

Synonyms:(1'S,3S)-1-(1'-naphthyl)ethyl methyl 3-(4-bromophenyl)pentanedioate

Chemical Property of (1'S,3S)-1-(1'-naphthyl)ethyl methyl 3-(4-bromophenyl)pentanedioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'S,3S)-1-(1'-naphthyl)ethyl methyl 3-(4-bromophenyl)pentanedioate

There total 4 articles about (1'S,3S)-1-(1'-naphthyl)ethyl methyl 3-(4-bromophenyl)pentanedioate 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: 87.0%

methanol (67-56-1) + (1'S,3S)-1'-naphthylethyl-4-(1-methyl-1H-imidazolylcarbonyl)-3-(4-bromophenyl)butyrate (1315282-20-2) → (1'S,3S)-1-(1'-naphthyl)ethyl methyl 3-(4-bromophenyl)pentanedioate (1315282-24-6)

Guidance literature:

(1'S,3S)-1'-naphthylethyl-4-(1-methyl-1H-imidazolylcarbonyl)-3-(4-bromophenyl)butyrate; With methyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 2.5h; Molecular sieve; Inert atmosphere;

methanol; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/anie.201102405

Reference yield:

3-(4-bromophenyl)-1-(1-methyl-1H-imidazol-2-yl)prop-2-en-1-one → (1'S,3S)-1-(1'-naphthyl)ethyl methyl 3-(4-bromophenyl)pentanedioate (1315282-24-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: silver hexafluoroantimonate; hexafluoropropan-2-ol; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; copper dichloride / dichloromethane / 72 h / -78 °C / Molecular sieve; Inert atmosphere

2.1: lithium hydroxide / tetrahydrofuran; water / 2 h / 0 - 20 °C / Inert atmosphere

3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: methyl trifluoromethanesulfonate / acetonitrile / 2.5 h / 20 °C / Molecular sieve; Inert atmosphere

4.2: 0.5 h / 20 °C / Inert atmosphere

With dmap; silver hexafluoroantimonate; hexafluoropropan-2-ol; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; methyl trifluoromethanesulfonate; copper dichloride; lithium hydroxide; In tetrahydrofuran; dichloromethane; water; acetonitrile; 1.1: Mukaiyama-Michael reaction;

DOI:10.1002/anie.201102405

Reference yield:

(3S)-4-(1-methyl-1H-imidazolylcarbonyl)-3-(4-bromophenyl)butyric acid (1315282-22-4) → (1'S,3S)-1-(1'-naphthyl)ethyl methyl 3-(4-bromophenyl)pentanedioate (1315282-24-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: methyl trifluoromethanesulfonate / acetonitrile / 2.5 h / 20 °C / Molecular sieve; Inert atmosphere

2.2: 0.5 h / 20 °C / Inert atmosphere

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; methyl trifluoromethanesulfonate; In dichloromethane; acetonitrile;

DOI:10.1002/anie.201102405

upstream raw materials:

methanol

(1'S,3S)-1'-naphthylethyl-4-(1-methyl-1H-imidazolylcarbonyl)-3-(4-bromophenyl)butyrate

C₂₄H₂₁BrN₄O₄

(3S)-4-(1-methyl-1H-imidazolylcarbonyl)-3-(4-bromophenyl)butyric acid