(R)-(-)-5-but-3-enyl-1-(toluene-4-sulfonyl)pyrrolidin-2-one

Base Information

• Chemical Name: (R)-(-)-5-but-3-enyl-1-(toluene-4-sulfonyl)pyrrolidin-2-one
• CAS No.: 853356-38-4
• Molecular Formula: C₁₅H₁₉NO₃S
• Molecular Weight: 293.387
• Mol file: 853356-38-4.mol

Synonyms:(R)-(-)-5-but-3-enyl-1-(toluene-4-sulfonyl)pyrrolidin-2-one

Chemical Property of (R)-(-)-5-but-3-enyl-1-(toluene-4-sulfonyl)pyrrolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-(-)-5-but-3-enyl-1-(toluene-4-sulfonyl)pyrrolidin-2-one

There total 3 articles about (R)-(-)-5-but-3-enyl-1-(toluene-4-sulfonyl)pyrrolidin-2-one 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: 59.0%

(R)-5-(but-3-en-1-yl)pyrrolidin-2-one (633294-91-4) + p-toluenesulfonyl chloride (98-59-9) → (R)-(-)-5-but-3-enyl-1-(toluene-4-sulfonyl)pyrrolidin-2-one (853356-38-4)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 3h;

DOI:10.1021/jo0504058

Reference yield:

(S)-Pyroglutaminol (17342-08-4) → (R)-(-)-5-but-3-enyl-1-(toluene-4-sulfonyl)pyrrolidin-2-one (853356-38-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 16 h / 20 °C

2: 61 percent / diethyl ether; tetrahydrofuran / 3 h / Heating

3: 59 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -78 - 20 °C

With dmap; n-butyllithium; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1021/jo0504058

Reference yield:

(S)-toluene-4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester (51693-17-5) → (R)-(-)-5-but-3-enyl-1-(toluene-4-sulfonyl)pyrrolidin-2-one (853356-38-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / diethyl ether; tetrahydrofuran / 3 h / Heating

2: 59 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -78 - 20 °C

With n-butyllithium; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1021/jo0504058

upstream raw materials:

(R)-5-(but-3-en-1-yl)pyrrolidin-2-one

p-toluenesulfonyl chloride

(S)-toluene-4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester

(S)-Pyroglutaminol

Downstream raw materials:

trifluoromethanesulfonic acid (R)-5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl ester

(R)-(-)-{2-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-2-oxoethyl}phosphonic acid dimethyl ester

(2R,4S)-(+)-2-but-3-enyl-4-isopropyl-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-cyclopenta[b]pyrrol-6-one

(R)-(-)-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-4-methylpent-2-en-1-one