(4R,5S,8R)-1-(4-methoxybenzyl)-4-hydroxy-5-[3-hydroxy-4-(3-(trifluoromethyl)phenyl)butyl]pyrrolidin-2-one

Base Information

Chemical Name:(4R,5S,8R)-1-(4-methoxybenzyl)-4-hydroxy-5-[3-hydroxy-4-(3-(trifluoromethyl)phenyl)butyl]pyrrolidin-2-one
CAS No.:1393803-35-4
Molecular Formula:C₂₃H₂₆F₃NO₄
Molecular Weight:437.459
Hs Code.:

Synonyms:(4R,5S,8R)-1-(4-methoxybenzyl)-4-hydroxy-5-[3-hydroxy-4-(3-(trifluoromethyl)phenyl)butyl]pyrrolidin-2-one

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Chemical Property of (4R,5S,8R)-1-(4-methoxybenzyl)-4-hydroxy-5-[3-hydroxy-4-(3-(trifluoromethyl)phenyl)butyl]pyrrolidin-2-one

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Technology Process of (4R,5S,8R)-1-(4-methoxybenzyl)-4-hydroxy-5-[3-hydroxy-4-(3-(trifluoromethyl)phenyl)butyl]pyrrolidin-2-one

There total 7 articles about (4R,5S,8R)-1-(4-methoxybenzyl)-4-hydroxy-5-[3-hydroxy-4-(3-(trifluoromethyl)phenyl)butyl]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: 90.0%

: 1393803-26-3
(4R,5S,8R)-1-(4-methoxybenzyl)-4-benzyloxy-5-[3-hydroxy-4-(3-(trifluoromethyl)phenyl)butyl]pyrrolidin-2-one

: 1393803-35-4
(4R,5S,8R)-1-(4-methoxybenzyl)-4-hydroxy-5-[3-hydroxy-4-(3-(trifluoromethyl)phenyl)butyl]pyrrolidin-2-one

Guidance literature:: With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 24h;
DOI:10.1021/jo301277n

Reference yield:

: 622833-72-1
(R)-1-(4-methoxybenzyl)-3-(benzyloxy)pyrrolidine-2,5-dione

: 1393803-35-4
(4R,5S,8R)-1-(4-methoxybenzyl)-4-hydroxy-5-[3-hydroxy-4-(3-(trifluoromethyl)phenyl)butyl]pyrrolidin-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium tetrahydroborate / methanol / 0.75 h / -15 °C

1.2: 5 h / 20 °C / Inert atmosphere

2.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4.5 h / 0 - 20 °C

3.1: samarium diiodide; tert-butyl alcohol / tetrahydrofuran / 0.17 h / -60 °C

4.1: trimethylaluminum / dichloromethane; toluene / 0 °C

4.2: 24 h / 20 °C

5.1: tetrahydrofuran; diethyl ether / -78 °C

6.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 25 h / -40 °C / Inert atmosphere

7.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C

With sodium tetrahydroborate; samarium diiodide; palladium 10% on activated carbon; hydrogen; trimethylaluminum; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; tert-butyl alcohol; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
DOI:10.1021/jo301277n

Reference yield:

: 1393803-25-2
(4R,5S)-1-(4-methoxybenzyl)-4-benzyloxy-5-[3-oxo-4-(3-(trifluoromethyl)phenyl)butyl]pyrrolidin-2-one

: 1393803-35-4
(4R,5S,8R)-1-(4-methoxybenzyl)-4-hydroxy-5-[3-hydroxy-4-(3-(trifluoromethyl)phenyl)butyl]pyrrolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 25 h / -40 °C / Inert atmosphere

2: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C

With palladium 10% on activated carbon; hydrogen; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; methanol;
DOI:10.1021/jo301277n