4-[bis-(4-methoxy-benzyl)-amino]-1,1a,6,6a-tetrahydro-3-aza-cyclopropa[a]-indene-1-carboxylic acid ethyl ester

Base Information

• Chemical Name: 4-[bis-(4-methoxy-benzyl)-amino]-1,1a,6,6a-tetrahydro-3-aza-cyclopropa[a]-indene-1-carboxylic acid ethyl ester
• CAS No.: 1544739-13-0
• Molecular Formula: C₂₈H₃₀N₂O₄
• Molecular Weight: 458.557
• Mol file: 1544739-13-0.mol

Synonyms:4-[bis-(4-methoxy-benzyl)-amino]-1,1a,6,6a-tetrahydro-3-aza-cyclopropa[a]-indene-1-carboxylic acid ethyl ester

Chemical Property of 4-[bis-(4-methoxy-benzyl)-amino]-1,1a,6,6a-tetrahydro-3-aza-cyclopropa[a]-indene-1-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[bis-(4-methoxy-benzyl)-amino]-1,1a,6,6a-tetrahydro-3-aza-cyclopropa[a]-indene-1-carboxylic acid ethyl ester

There total 1 articles about 4-[bis-(4-methoxy-benzyl)-amino]-1,1a,6,6a-tetrahydro-3-aza-cyclopropa[a]-indene-1-carboxylic acid ethyl 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:

diazoacetic acid ethyl ester (623-73-4) + bis-(4-methoxy-benzyl)-(5H-[2]pyrindin-3-yl)-amine (1544739-12-9) → 4-[bis-(4-methoxy-benzyl)-amino]-1,1a,6,6a-tetrahydro-3-aza-cyclopropa[a]-indene-1-carboxylic acid ethyl ester (1544739-13-0)

Guidance literature:

bis-(4-methoxy-benzyl)-(5H-[2]pyrindin-3-yl)-amine; With rhodium(II) acetate; In dichloromethane; for 0.25h;

diazoacetic acid ethyl ester; In dichloromethane; for 3h; Reflux;

Reference yield:

4-[bis-(4-methoxy-benzyl)-amino]-1,1a,6,6a-tetrahydro-3-aza-cyclopropa[a]-indene-1-carboxylic acid ethyl ester (1544739-13-0) → (5aR,6S,6aS)-ethyl 3-((2’,4-difluoro-4’-(3-(methylsulfonyl)propoxy)-6’-(trifluoromethyl)-[1,1‘-biphenyl]-3-yl)methoxy)-5,5a,6,6a-tetrahydrocyclopropa[4,5]-cyclopenta[1,2-c]pyridine-6-carboxylate (1544739-74-3)

Guidance literature:

Multi-step reaction with 4 steps

1: trifluoroacetic acid / dichloromethane / 20 °C

2: sulfuric acid; sodium nitrite / 2 h / 0 - 20 °C

3: silver carbonate / toluene / 110 °C / Inert atmosphere

4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / tetrahydrofuran; water / 0.17 h / 100 °C / Inert atmosphere; Sealed tube; Microwave irradiation

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; sulfuric acid; silver carbonate; trifluoroacetic acid; sodium nitrite; In tetrahydrofuran; dichloromethane; water; toluene;

Reference yield:

4-[bis-(4-methoxy-benzyl)-amino]-1,1a,6,6a-tetrahydro-3-aza-cyclopropa[a]-indene-1-carboxylic acid ethyl ester (1544739-13-0) → (5aR,6S,6aS)-ethyl 3-((4-fluoro-4’-((S)-2-hydroxypropoxy)-2’,6’-dimethyl-[1,1’-biphenyl]-3-yl)methoxy)-5,5a,6,6a-tetrahydrocyclopropa[4,5]cyclopenta[1,2-c]pyridine-6-carboxylate (1544739-49-2)

Guidance literature:

Multi-step reaction with 4 steps

1: trifluoroacetic acid / dichloromethane / 20 °C

2: sulfuric acid; sodium nitrite / 2 h / 0 - 20 °C

3: silver carbonate / toluene / 110 °C / Inert atmosphere

4: potassium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine / water; 1,4-dioxane / 0.17 h / 130 °C / Inert atmosphere; Microwave irradiation

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sulfuric acid; potassium carbonate; silver carbonate; trifluoroacetic acid; sodium nitrite; tricyclohexylphosphine; In 1,4-dioxane; dichloromethane; water; toluene;

upstream raw materials:

diazoacetic acid ethyl ester

bis-(4-methoxy-benzyl)-(5H-[2]pyrindin-3-yl)-amine

Downstream raw materials:

(5aR,6S,6aS)-ethyl 3-((4-fluoro-4’-((S)-2-hydroxypropoxy)-2’,6’-dimethyl-[1,1’-biphenyl]-3-yl)methoxy)-5,5a,6,6a-tetrahydrocyclopropa[4,5]cyclopenta[1,2-c]pyridine-6-carboxylate

(5aR,6S,6aS)-3-((4-fluoro-4’-((S)-2-hydroxypropoxy)-2’,6’-dimethyl-[1,1‘-biphenyl]-3-yl)methoxy)-5,5a,6,6a-tetrahydrocyclopropa[4,5]cyclopenta[1,2-c]pyridine-6-carboxylic acid

(5aR,6S,6aS)-ethyl 3-((4-fluoro-4’-(2-(1-hydroxycyclopropyl)ethoxy)-2’-(trifluoromethyl)-[1,1‘-biphenyl]-3-yl)methoxy)-5,5a,6,6a-tetrahydrocyclopropa[4,5]-cyclopenta[1,2-c]pyridine-6-carboxylate

(5aR,6S,6aS)-3-((4-fluoro-4’-(2-(1-hydroxycyclopropyl)ethoxy)-2’-(trifluoromethyl)-[1,1‘-biphenyl]-3-yl)methoxy)-5,5a,6,6a-tetrahydrocyclopropa[4,5]cyclopenta[1,2-c]pyridine-6-carboxylic acid