(+)-trans-N-[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-nitro-benzenesulfonamide

Base Information

• Chemical Name: (+)-trans-N-[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-nitro-benzenesulfonamide
• CAS No.: 1369217-04-8
• Molecular Formula: C₂₃H₂₁ClN₂O₅S
• Molecular Weight: 472.949
• Mol file: 1369217-04-8.mol

Synonyms:(+)-trans-N-[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-nitro-benzenesulfonamide

Chemical Property of (+)-trans-N-[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-nitro-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-trans-N-[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-nitro-benzenesulfonamide

There total 6 articles about (+)-trans-N-[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-nitro-benzenesulfonamide 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:

1-chloro-2-methoxy-4-(4-phenyl-but-1-enyl)-benzene (1369217-06-0) + [N-(nosyl)imino]phenyliodinane (149552-43-2) → (+)-trans-N-[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-nitro-benzenesulfonamide (1369217-04-8) + (-)-trans-N-[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-nitro-benzenesulfonamide (1369217-09-3)

Guidance literature:

1-chloro-2-methoxy-4-(4-phenyl-but-1-enyl)-benzene; [N-(nosyl)imino]phenyliodinane; With copper(II) bis(trifluoromethanesulfonate); (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline); In dichloromethane; at 25 ℃; for 1h; Inert atmosphere; Molecular sieve;

With copper(II) bis(trifluoromethanesulfonate); In dichloromethane; at 25 ℃; for 1h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1016/j.tetasy.2012.01.017

Reference yield:

1-chloro-2-methoxy-4-(4-phenyl-but-1-enyl)-benzene + [N-(nosyl)imino]phenyliodinane (149552-43-2) → (+)-trans-N-[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-nitro-benzenesulfonamide (1369217-04-8) + (-)-trans-N-[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-nitro-benzenesulfonamide (1369217-09-3)

Guidance literature:

1-chloro-2-methoxy-4-(4-phenyl-but-1-enyl)-benzene; [N-(nosyl)imino]phenyliodinane; With copper(II) bis(trifluoromethanesulfonate); (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline); In dichloromethane; at 32 ℃; for 3h; Inert atmosphere; Molecular sieve;

With copper(II) bis(trifluoromethanesulfonate); In dichloromethane; at 32 ℃; for 1h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1016/j.tetasy.2012.01.017

Reference yield:

3-phenyl-propionaldehyde (104-53-0) → (+)-trans-N-[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-nitro-benzenesulfonamide (1369217-04-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 - 20 °C / Inert atmosphere

2.1: copper(II) bis(trifluoromethanesulfonate); (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline) / dichloromethane / 3 h / 32 °C / Inert atmosphere; Molecular sieve

2.2: 1 h / 32 °C / Inert atmosphere

With n-butyllithium; copper(II) bis(trifluoromethanesulfonate); (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline); In tetrahydrofuran; hexane; dichloromethane; 1.2: Wittig reaction / 2.2: Friedel Crafts alkylation;

DOI:10.1016/j.tetasy.2012.01.017

upstream raw materials:

3-phenyl-propionaldehyde

[N-(nosyl)imino]phenyliodinane

1-chloro-2-methoxy-4-(4-phenyl-but-1-enyl)-benzene

4-Phenyl-1-butyne

Downstream raw materials:

{[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-methyl-amino}-acetic acid methyl ester

(+)-trans-N-[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-methylamine

ecopipam

C₂₄H₂₃ClN₂O₅S