(3R,4R)-4-(4-chlorostyryl)-3-methyl-3-(prop-1-en-2-yl)-1-tosylpyrrolidine

Base Information

• Chemical Name: (3R,4R)-4-(4-chlorostyryl)-3-methyl-3-(prop-1-en-2-yl)-1-tosylpyrrolidine
• CAS No.: 1285257-03-5
• Molecular Formula: C₂₃H₂₆ClNO₂S
• Molecular Weight: 415.984
• Mol file: 1285257-03-5.mol

Synonyms:

Chemical Property of (3R,4R)-4-(4-chlorostyryl)-3-methyl-3-(prop-1-en-2-yl)-1-tosylpyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-4-(4-chlorostyryl)-3-methyl-3-(prop-1-en-2-yl)-1-tosylpyrrolidine

There total 5 articles about (3R,4R)-4-(4-chlorostyryl)-3-methyl-3-(prop-1-en-2-yl)-1-tosylpyrrolidine 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:

(E)-N-(4-(4-chlorophenyl)but-3-enyl)-4-methyl-N-(3-methyl-2-methylenebut-3-enyl)benzenesulfonamide (1285256-92-9) → (3R,4R)-4-(4-chlorostyryl)-3-methyl-3-(prop-1-en-2-yl)-1-tosylpyrrolidine (1285257-03-5) + (3S,4S)-4-(4-chlorostyryl)-3-methyl-3-(prop-1-en-2-yl)-1-tosylpyrrolidine

Guidance literature:

With chlorobis(cyclooctene)rhodium(I) dimer; silver trifluoromethanesulfonate; (S)-(+)-(3,5-dioxa-4-phosphacyclohepta[2,1-a:3,4-a']dinaphthalen-4-yl)diethylamine; In 1,2-dimethoxyethane; at 80 ℃; for 11h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201005215

Reference yield:

C22H26ClNO4S → (3R,4R)-4-(4-chlorostyryl)-3-methyl-3-(prop-1-en-2-yl)-1-tosylpyrrolidine (1285257-03-5) + (3S,4S)-4-(4-chlorostyryl)-3-methyl-3-(prop-1-en-2-yl)-1-tosylpyrrolidine

Guidance literature:

Multi-step reaction with 3 steps

1.1: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C / Inert atmosphere

2.2: 1.5 h / 20 °C / Inert atmosphere

3.1: chlorobis(cyclooctene)rhodium(I) dimer; silver trifluoromethanesulfonate; (S)-(+)-(3,5-dioxa-4-phosphacyclohepta[2,1-a:3,4-a']dinaphthalen-4-yl)diethylamine / 1,2-dimethoxyethane / 11 h / 80 °C / Inert atmosphere

With chlorobis(cyclooctene)rhodium(I) dimer; silver trifluoromethanesulfonate; sodium hydride; trifluoroacetic acid; (S)-(+)-(3,5-dioxa-4-phosphacyclohepta[2,1-a:3,4-a']dinaphthalen-4-yl)diethylamine; In 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.201005215

Reference yield:

N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide (18303-04-3) → (3R,4R)-4-(4-chlorostyryl)-3-methyl-3-(prop-1-en-2-yl)-1-tosylpyrrolidine (1285257-03-5) + (3S,4S)-4-(4-chlorostyryl)-3-methyl-3-(prop-1-en-2-yl)-1-tosylpyrrolidine

Guidance literature:

Multi-step reaction with 4 steps

1.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 3 h / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C / Inert atmosphere

3.2: 1.5 h / 20 °C / Inert atmosphere

4.1: chlorobis(cyclooctene)rhodium(I) dimer; silver trifluoromethanesulfonate; (S)-(+)-(3,5-dioxa-4-phosphacyclohepta[2,1-a:3,4-a']dinaphthalen-4-yl)diethylamine / 1,2-dimethoxyethane / 11 h / 80 °C / Inert atmosphere

With chlorobis(cyclooctene)rhodium(I) dimer; silver trifluoromethanesulfonate; sodium hydride; triphenylphosphine; trifluoroacetic acid; (S)-(+)-(3,5-dioxa-4-phosphacyclohepta[2,1-a:3,4-a']dinaphthalen-4-yl)diethylamine; diethylazodicarboxylate; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.201005215

upstream raw materials:

C₁₃H₁₆O₃S

(E)-N-(4-(4-chlorophenyl)but-3-enyl)-4-methyl-N-(3-methyl-2-methylenebut-3-enyl)benzenesulfonamide

N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide

(E/Z)-4-(4-chlorophenyl)but-3-en-1-ol