(E)-3-(1'-benzyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-6-yl)-acrylic acid methyl ester

Base Information

• Chemical Name: (E)-3-(1'-benzyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-6-yl)-acrylic acid methyl ester
• CAS No.: 1192128-27-0
• Molecular Formula: C₂₃H₂₄N₂O₄
• Molecular Weight: 392.455
• Mol file: 1192128-27-0.mol

Synonyms:(E)-3-(1'-benzyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-6-yl)-acrylic acid methyl ester

Chemical Property of (E)-3-(1'-benzyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-6-yl)-acrylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-(1'-benzyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-6-yl)-acrylic acid methyl ester

There total 4 articles about (E)-3-(1'-benzyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-6-yl)-acrylic acid methyl 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:

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → (E)-3-(1'-benzyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-6-yl)-acrylic acid methyl ester (1192128-27-0)

Guidance literature:

Multi-step reaction with 4 steps

1: pyrrolidine / 2 h / 72 °C / Microwave irradiation

2: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 9 h / 100 °C / Inert atmosphere

3: hydrogenchloride / 1,4-dioxane; dichloromethane / 4 h / 20 °C

4: triethylamine / dichloromethane / 5 h / 20 °C

With pyrrolidine; hydrogenchloride; palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 2: |Heck Reaction;

DOI:10.1016/j.ejmech.2013.03.061

Reference yield:

(E)-3-{1'-tert-butoxycarbonyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-6-yl}-acrylic acid methyl ester (1192127-62-0) → (E)-3-(1'-benzyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-6-yl)-acrylic acid methyl ester (1192128-27-0)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / 1,4-dioxane; dichloromethane / 4 h / 20 °C

2: triethylamine / dichloromethane / 5 h / 20 °C

With hydrogenchloride; triethylamine; In 1,4-dioxane; dichloromethane;

DOI:10.1016/j.ejmech.2013.03.061

Reference yield:

6-bromo-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-1'-carboxylic acid tert-butyl ester (690632-05-4) → (E)-3-(1'-benzyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-6-yl)-acrylic acid methyl ester (1192128-27-0)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 9 h / 100 °C / Inert atmosphere

2: hydrogenchloride / 1,4-dioxane; dichloromethane / 4 h / 20 °C

3: triethylamine / dichloromethane / 5 h / 20 °C

With hydrogenchloride; palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 1: |Heck Reaction;

DOI:10.1016/j.ejmech.2013.03.061

upstream raw materials:

N-tert-butyloxycarbonylpiperidin-4-one

(E)-3-{1'-tert-butoxycarbonyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-6-yl}-acrylic acid methyl ester

6-bromo-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-1'-carboxylic acid tert-butyl ester

5-bromo-2-hydroxybenzamide

Downstream raw materials:

(E)-3-{1'-benzyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-6-yl}-acrylic acid

(E)-3-(1'-benzyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-6-yl)-N-(tetrahydro-pyran-2-yloxy)-acrylamide