(R)-6-[(E)-4-(3,4-dimethoxyphenyl)-2-oxobut-3-enyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

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Chemical Name:(R)-6-[(E)-4-(3,4-dimethoxyphenyl)-2-oxobut-3-enyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester
CAS No.:791821-98-2
Molecular Formula:C₂₂H₂₉NO₅
Molecular Weight:387.476
Hs Code.:

Synonyms:(R)-6-[(E)-4-(3,4-dimethoxyphenyl)-2-oxobut-3-enyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

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Chemical Property of (R)-6-[(E)-4-(3,4-dimethoxyphenyl)-2-oxobut-3-enyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

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Technology Process of (R)-6-[(E)-4-(3,4-dimethoxyphenyl)-2-oxobut-3-enyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

There total 6 articles about (R)-6-[(E)-4-(3,4-dimethoxyphenyl)-2-oxobut-3-enyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 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%

: 6380-23-0
3,4-dimethoxystyrene

: 791821-99-3
but-3-enyl-((R)-4-oxocyclopent-2-enyl)carbamic acid tert-butyl ester

: 791821-98-2
(R)-6-[(E)-4-(3,4-dimethoxyphenyl)-2-oxobut-3-enyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Guidance literature:: With [1,3-Mes₂-(N₂C₃H₅)]Cl₂(PCy₃)Ru=CHPh; In dichloromethane; for 12h; Heating;
DOI:10.1016/j.tet.2004.06.145

Reference yield:

: (1S,4R)-4-But-3-enylamino-cyclopent-2-enol

: 791821-98-2
(R)-6-[(E)-4-(3,4-dimethoxyphenyl)-2-oxobut-3-enyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 3.05 g / Et₃N / methanol / 4 h / 70 °C

2: 99 percent / imidazole / dimethylformamide / 50 h / 20 °C

3: 98 percent / ethylene; Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 57 h / 20 °C

4: 96 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

5: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

6: 1.65 g / [1,3-Mes₂-(N₂C₃H₅)]Cl₂Ru=CH(2-isopropoxyphenyl) / CH₂Cl₂ / 14 h / Heating

With 1H-imidazole; Grubbs catalyst first generation; ethene; [1,3-Mes₂-(N₂C₃H₅)]Cl₂Ru=CH(2-isopropoxyphenyl); tetrabutyl ammonium fluoride; Dess-Martin periodane; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 5: Dess-Martin oxidation;
DOI:10.1016/j.tet.2004.06.145

Reference yield:

: 791821-96-0
but-3-enyl-((1R,4S)-4-hydroxycyclopent-2-enyl)carbamic acid tert-butyl ester

: 791821-98-2
(R)-6-[(E)-4-(3,4-dimethoxyphenyl)-2-oxobut-3-enyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / imidazole / dimethylformamide / 50 h / 20 °C

2: 98 percent / ethylene; Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 57 h / 20 °C

3: 96 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

4: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

5: 1.65 g / [1,3-Mes₂-(N₂C₃H₅)]Cl₂Ru=CH(2-isopropoxyphenyl) / CH₂Cl₂ / 14 h / Heating

With 1H-imidazole; Grubbs catalyst first generation; ethene; [1,3-Mes₂-(N₂C₃H₅)]Cl₂Ru=CH(2-isopropoxyphenyl); tetrabutyl ammonium fluoride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 4: Dess-Martin oxidation;
DOI:10.1016/j.tet.2004.06.145