(S)-N-(2-(3,4-dimethoxyphenoxy)ethyl)-6-oxo-N-(4-(trimethylsilyl)but-2-en-1-yl)piperidine-2-carboxamide

Base Information

Chemical Name:(S)-N-(2-(3,4-dimethoxyphenoxy)ethyl)-6-oxo-N-(4-(trimethylsilyl)but-2-en-1-yl)piperidine-2-carboxamide
CAS No.:1542785-98-7
Molecular Formula:C₂₃H₃₆N₂O₅Si
Molecular Weight:448.635
Hs Code.:

Synonyms:(S)-N-(2-(3,4-dimethoxyphenoxy)ethyl)-6-oxo-N-(4-(trimethylsilyl)but-2-en-1-yl)piperidine-2-carboxamide

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Chemical Property of (S)-N-(2-(3,4-dimethoxyphenoxy)ethyl)-6-oxo-N-(4-(trimethylsilyl)but-2-en-1-yl)piperidine-2-carboxamide

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Technology Process of (S)-N-(2-(3,4-dimethoxyphenoxy)ethyl)-6-oxo-N-(4-(trimethylsilyl)but-2-en-1-yl)piperidine-2-carboxamide

There total 8 articles about (S)-N-(2-(3,4-dimethoxyphenoxy)ethyl)-6-oxo-N-(4-(trimethylsilyl)but-2-en-1-yl)piperidine-2-carboxamide 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%

: 1542785-96-5
N-(2-(3,4-dimethoxyphenoxy)ethyl)-4-(trimethylsilyl)but-2-en-1-amine

: 34622-39-4
(2S)-6-oxopipecolic acid

: 1542785-98-7
(S)-N-(2-(3,4-dimethoxyphenoxy)ethyl)-6-oxo-N-(4-(trimethylsilyl)but-2-en-1-yl)piperidine-2-carboxamide

Guidance literature:: (2S)-6-oxopipecolic acid; With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 0.5h;

N-(2-(3,4-dimethoxyphenoxy)ethyl)-4-(trimethylsilyl)but-2-en-1-amine; In dichloromethane; for 24h;

Reference yield:

: 2033-77-4
4-(2-bromoethoxy)-1,2-dimethoxybenzene

: 1542785-98-7
(S)-N-(2-(3,4-dimethoxyphenoxy)ethyl)-6-oxo-N-(4-(trimethylsilyl)but-2-en-1-yl)piperidine-2-carboxamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

1.2: 2 h / 0 °C / Inert atmosphere

2.1: Grubbs catalyst first generation / dichloromethane / Reflux

3.1: silica gel / 2 h / 150 °C

4.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 °C

4.2: 24 h

With Grubbs catalyst first generation; 1-hydroxy-7-aza-benzotriazole; silica gel; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

Reference yield:

: N-(2-(3,4-dimethoxyphenoxy)ethyl)prop-2-en-1-amine

: 1542785-98-7
(S)-N-(2-(3,4-dimethoxyphenoxy)ethyl)-6-oxo-N-(4-(trimethylsilyl)but-2-en-1-yl)piperidine-2-carboxamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere

2.1: p-benzoquinone; Hoveyda-Grubbs catalyst second generation / dichloromethane / 4 h / 60 °C / Inert atmosphere

2.2: 12 h / Inert atmosphere; Reflux

3.1: potassium carbonate; thiophenol / N,N-dimethyl-formamide / 14 h / 20 °C / Inert atmosphere

4.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

With Hoveyda-Grubbs catalyst second generation; potassium carbonate; thiophenol; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; p-benzoquinone; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/anie.201408776