(2R,8aR)-2-hydroxy-6-phenyl-7-(4-bromophenyl)-2,3,8,8a-tetrahydroindolizin-5(1H)-one

Base Information

Chemical Name:(2R,8aR)-2-hydroxy-6-phenyl-7-(4-bromophenyl)-2,3,8,8a-tetrahydroindolizin-5(1H)-one
CAS No.:1375571-10-0
Molecular Formula:C₂₀H₁₈BrNO₂
Molecular Weight:384.272
Hs Code.:

Synonyms:(2R,8aR)-2-hydroxy-6-phenyl-7-(4-bromophenyl)-2,3,8,8a-tetrahydroindolizin-5(1H)-one

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Chemical Property of (2R,8aR)-2-hydroxy-6-phenyl-7-(4-bromophenyl)-2,3,8,8a-tetrahydroindolizin-5(1H)-one

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Technology Process of (2R,8aR)-2-hydroxy-6-phenyl-7-(4-bromophenyl)-2,3,8,8a-tetrahydroindolizin-5(1H)-one

There total 9 articles about (2R,8aR)-2-hydroxy-6-phenyl-7-(4-bromophenyl)-2,3,8,8a-tetrahydroindolizin-5(1H)-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: 48.0%

: 1375570-92-5
(2R,4R)-4-(acetoxy)-2-(2-[4-bromophenyl]-2-oxoethyl)-1-(2-phenylacetyl)pyrrolidine

: 1375571-10-0
(2R,8aR)-2-hydroxy-6-phenyl-7-(4-bromophenyl)-2,3,8,8a-tetrahydroindolizin-5(1H)-one

: 1375571-12-2
(2R,8aS)-2-hydroxy-6-phenyl-7-(4-bromophenyl)-2,3,8,8a-tetrahydroindolizin-5(1H)-one

Guidance literature:: With methanol; potassium hydroxide; at 65 ℃; for 4h;
DOI:10.1016/j.bmcl.2012.03.109

Reference yield:

: benzyl (2S,4R)-4-(acetoxy)-1-(2-phenylacetyl)proline

: 1375571-10-0
(2R,8aR)-2-hydroxy-6-phenyl-7-(4-bromophenyl)-2,3,8,8a-tetrahydroindolizin-5(1H)-one

: 1375571-12-2
(2R,8aS)-2-hydroxy-6-phenyl-7-(4-bromophenyl)-2,3,8,8a-tetrahydroindolizin-5(1H)-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h

2.1: [bis(acetoxy)iodo]benzene; iodine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Irradiation

2.2: 1.5 h / 0 °C / Inert atmosphere

3.1: potassium hydroxide / methanol / 4 h / Reflux

With [bis(acetoxy)iodo]benzene; palladium 10% on activated carbon; hydrogen; iodine; potassium hydroxide; In methanol; dichloromethane; ethyl acetate;
DOI:10.1016/j.ejmech.2013.06.009

Reference yield:

: 51-35-4,30724-02-8
4R-4-hydroxyproline

: 1375571-10-0
(2R,8aR)-2-hydroxy-6-phenyl-7-(4-bromophenyl)-2,3,8,8a-tetrahydroindolizin-5(1H)-one

: 1375571-12-2
(2R,8aS)-2-hydroxy-6-phenyl-7-(4-bromophenyl)-2,3,8,8a-tetrahydroindolizin-5(1H)-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: p-toluenesulfonic acid monohydrate / toluene / Reflux

2.1: toluene / 26 °C

3.1: pyridine / 12 h / 0 - 26 °C

4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h

5.1: [bis(acetoxy)iodo]benzene; iodine / dichloromethane / 3 h / 26 °C / Inert atmosphere; Irradiation

5.2: 1.5 h / 0 °C / Inert atmosphere

6.1: potassium hydroxide / methanol / 4 h / Reflux

With pyridine; [bis(acetoxy)iodo]benzene; palladium 10% on activated carbon; p-toluenesulfonic acid monohydrate; hydrogen; iodine; potassium hydroxide; In methanol; dichloromethane; ethyl acetate; toluene;
DOI:10.1016/j.ejmech.2013.06.009