(S)-1,2,3,5,8,8a-hexahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizine

Base Information

• Chemical Name: (S)-1,2,3,5,8,8a-hexahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizine
• CAS No.: 1242597-79-0
• Molecular Formula: C₂₃H₂₇NO₃
• Molecular Weight: 365.472
• Mol file: 1242597-79-0.mol

Synonyms:(S)-1,2,3,5,8,8a-hexahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizine

Chemical Property of (S)-1,2,3,5,8,8a-hexahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1,2,3,5,8,8a-hexahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizine

There total 23 articles about (S)-1,2,3,5,8,8a-hexahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizine 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: 96.0%

4-Bromoveratrole (2859-78-1) + (S)-6-(4-methoxyphenyl)-1,2,3,5,8,8a-hexahydroindolizin-7-yl trifluoromethanesulfonate (1242597-71-2) → (S)-1,2,3,5,8,8a-hexahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizine (1242597-79-0)

Guidance literature:

4-Bromoveratrole; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 2h; Inert atmosphere;

With zinc dibromide; In tetrahydrofuran; pentane; at -78 - 20 ℃; Inert atmosphere;

(S)-6-(4-methoxyphenyl)-1,2,3,5,8,8a-hexahydroindolizin-7-yl trifluoromethanesulfonate; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; pentane; at 20 - 50 ℃; Inert atmosphere;

DOI:10.1021/jo101051w

Reference yield: 79.0%

(S)-1,2,8,8a-tetrahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizin-3(5H)-one (1301743-53-2) → (S)-1,2,3,5,8,8a-hexahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizine (1242597-79-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 25h;

DOI:10.1002/ejoc.201100125

Reference yield: 60.0%

4-Methoxyphenylacetaldehyde (5703-26-4) + (S)-tert-butyl 2-(2-(3,4-dimethoxyphenyl)-2-oxoethyl)pyrrolidine-1-carboxylate (138596-88-0) → (S)-1,2,3,5,8,8a-hexahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizine (1242597-79-0)

Guidance literature:

(S)-tert-butyl 2-(2-(3,4-dimethoxyphenyl)-2-oxoethyl)pyrrolidine-1-carboxylate; With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;

4-Methoxyphenylacetaldehyde; In benzene; at 0 - 20 ℃; for 5h; Inert atmosphere;

With sodium tetrahydroborate; In methanol; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ol403229q

upstream raw materials:

4-Bromoveratrole

(S)-6-(4-methoxyphenyl)-1,2,3,5,8,8a-hexahydroindolizin-7-yl trifluoromethanesulfonate

(6R,8aS)-hexahydro-6-(4-methoxyphenyl)indolizine-3,7-dione

(S)-1,2,3,5,8,8a-hexahydro-6-(4-methoxyphenyl)-3-oxoindolizin-7-yl-trifluoromethanesulfonate