(S)-1,2,8,8a-tetrahydro-6,7-bis(3,4-dimethoxyphenyl)-indolizin-3(5H)-one

Base Information

• Chemical Name: (S)-1,2,8,8a-tetrahydro-6,7-bis(3,4-dimethoxyphenyl)-indolizin-3(5H)-one
• CAS No.: 1446846-74-7
• Molecular Formula: C₂₄H₂₇NO₅
• Molecular Weight: 409.482
• Mol file: 1446846-74-7.mol

Synonyms:(S)-1,2,8,8a-tetrahydro-6,7-bis(3,4-dimethoxyphenyl)-indolizin-3(5H)-one

Chemical Property of (S)-1,2,8,8a-tetrahydro-6,7-bis(3,4-dimethoxyphenyl)-indolizin-3(5H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1,2,8,8a-tetrahydro-6,7-bis(3,4-dimethoxyphenyl)-indolizin-3(5H)-one

There total 11 articles about (S)-1,2,8,8a-tetrahydro-6,7-bis(3,4-dimethoxyphenyl)-indolizin-3(5H)-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: 81.0%

(S)-5-bis-[2-(3,4-dimethoxy-phenyl)-2-oxo-ethyl]-pyrrolidin-2-one → (S)-1,2,8,8a-tetrahydro-6,7-bis(3,4-dimethoxyphenyl)-indolizin-3(5H)-one (1446846-74-7)

Guidance literature:

With titanium tetrachloride; zinc; In tetrahydrofuran; at 68 ℃; for 24h; Inert atmosphere;

DOI:10.1080/00397911.2012.736004

Reference yield:

(8aS)-6,7-bis(3,4-dimethoxyphenyl)-8-hydroxy-1,5,8,8a-tetrahydroindolizin-3(2H)-one → (S)-1,2,8,8a-tetrahydro-6,7-bis(3,4-dimethoxyphenyl)-indolizin-3(5H)-one (1446846-74-7)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/acs.orglett.9b04479

Reference yield:

3,4-dimethoxy-benzaldehyde (120-14-9) → (S)-1,2,8,8a-tetrahydro-6,7-bis(3,4-dimethoxyphenyl)-indolizin-3(5H)-one (1446846-74-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C / Inert atmosphere

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

2.2: -78 - -25 °C / Inert atmosphere

3.1: mercury(II) oxide; mercury dichloride; water / acetonitrile / 16 h / 20 °C / Inert atmosphere

4.1: titanium tetrachloride; zinc / tetrahydrofuran / 24 h / 68 °C / Inert atmosphere

With n-butyllithium; boron trifluoride diethyl etherate; water; titanium tetrachloride; mercury dichloride; mercury(II) oxide; zinc; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; 4.1: |McMurry Reaction;

DOI:10.1080/00397911.2012.736004

upstream raw materials:

(S)-1,5-bis((2-(3,4-dimethoxyphenyl)-1,3-dithian-2-yl)methyl)pyrrolidin-2-one

3,4-dimethoxy-benzaldehyde

2-(3,4-dimethoxyphenyl)-1,3-dithiane

2,2-dibromo-1-(3,4-dimethoxyphenyl)ethene

Downstream raw materials:

(S)-1,2,3,5,8,8a-hexahydro-6,7-bis(3,4-dimethoxy-phenyl)indolizine