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

Base Information

• Chemical Name: (R)-(-)-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-4-methylpent-2-en-1-one
• CAS No.: 853356-37-3
• Molecular Formula: C₂₁H₂₇NO₃S
• Molecular Weight: 373.516
• Mol file: 853356-37-3.mol

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

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

There total 10 articles about (R)-(-)-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-4-methylpent-2-en-1-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: 68.0%

(R)-(-)-{2-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-2-oxoethyl}phosphonic acid dimethyl ester (853356-48-6) + isobutyraldehyde (78-84-2) → (R)-(-)-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-4-methylpent-2-en-1-one (853356-37-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile; at 25 ℃; for 24h;

DOI:10.1021/jo0504058

Reference yield: 24.0%

trifluoromethanesulfonic acid (R)-5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl ester (853356-39-5) + 4-methyl-2-pentenoyl chloride (18802-96-5,119163-26-7,40794-19-2) → (R)-(-)-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-4-methylpent-2-en-1-one (853356-37-3)

Guidance literature:

trifluoromethanesulfonic acid (R)-5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl ester; With triphenyl-arsane; hexamethyldistannane; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; at 40 ℃; for 4h;

4-methyl-2-pentenoyl chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; for 4h; Heating;

DOI:10.1021/jo0504058

Reference yield:

(S)-Pyroglutaminol (17342-08-4) → (R)-(-)-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-4-methylpent-2-en-1-one (853356-37-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 64 percent / 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 16 h / 20 °C

2.1: 61 percent / diethyl ether; tetrahydrofuran / 3 h / Heating

3.1: 59 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -78 - 20 °C

4.1: KHMDS / toluene; tetrahydrofuran / 1.5 h / -78 °C

4.2: toluene; tetrahydrofuran / 1 h / -78 °C

5.1: 65 percent / PPh₃; Et₃N / Pd(OAc)2 / dimethylformamide / 4 h / 40 °C

6.1: 41 percent / n-BuLi / hexane; tetrahydrofuran / 4 h / 25 °C

7.1: 68 percent / DIPEA; LiCl / acetonitrile / 24 h / 25 °C

With dmap; n-butyllithium; potassium hexamethylsilazane; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; palladium diacetate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 6.1: Horner-Emmons-Wadsworth reaction;

DOI:10.1021/jo0504058

upstream raw materials:

4-methyl-2-pentenoyl chloride

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

isobutyraldehyde

Downstream raw materials:

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