benzyl 8-methyl-9-oxo-3-azaspiro[5.5]undecane-3-carboxylate

Base Information

• Chemical Name: benzyl 8-methyl-9-oxo-3-azaspiro[5.5]undecane-3-carboxylate
• CAS No.: 1599479-09-0
• Molecular Formula: C₁₉H₂₅NO₃
• Molecular Weight: 315.412
• Mol file: 1599479-09-0.mol

Synonyms:benzyl 8-methyl-9-oxo-3-azaspiro[5.5]undecane-3-carboxylate

Chemical Property of benzyl 8-methyl-9-oxo-3-azaspiro[5.5]undecane-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 8-methyl-9-oxo-3-azaspiro[5.5]undecane-3-carboxylate

There total 1 articles about benzyl 8-methyl-9-oxo-3-azaspiro[5.5]undecane-3-carboxylate 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:

3-azaspiro[5.5]undecane-3-carboxylic acid, 9-oxo, phenylmethyl ester (1056629-20-9) + methyl iodide (74-88-4) → benzyl 8-methyl-9-oxo-3-azaspiro[5.5]undecane-3-carboxylate (1599479-09-0)

Guidance literature:

3-azaspiro[5.5]undecane-3-carboxylic acid, 9-oxo, phenylmethyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

methyl iodide; In tetrahydrofuran; at -78 - 20 ℃; for 2.5h;

Reference yield:

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + benzyl 8-methyl-9-oxo-3-azaspiro[5.5]undecane-3-carboxylate (1599479-09-0) → benzyl 9-(2-ethoxy-2-oxoethylidene)-8-methyl-3-azaspiro[5.5]undecane-3-carboxylate

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.5h;

benzyl 8-methyl-9-oxo-3-azaspiro[5.5]undecane-3-carboxylate; In tetrahydrofuran; at 20 ℃;

Reference yield:

benzyl 8-methyl-9-oxo-3-azaspiro[5.5]undecane-3-carboxylate (1599479-09-0) → ethyl 2-(3-(2-chloro-5-(trifluoromethoxy)phenyl)-8-methyl-3-azaspiro[5.5]undecan-9-yl)acetate (1599479-13-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C

1.2: 20 °C

2.1: 20% palladium hydroxide-activated charcoal; hydrogen / ethyl acetate

3.1: chloro(2-dicyclohexylphosphino-2′,6′-di-i-propoxy-1,1′-biphenyl)(2′-amino-1,1′-biphenyl-2-yl)-palladium(II); caesium carbonate / 1,4-dioxane / 100 °C / Microwave irradiation; Inert atmosphere; Sealed tube

With chloro(2-dicyclohexylphosphino-2′,6′-di-i-propoxy-1,1′-biphenyl)(2′-amino-1,1′-biphenyl-2-yl)-palladium(II); 20% palladium hydroxide-activated charcoal; hydrogen; sodium hydride; caesium carbonate; In tetrahydrofuran; 1,4-dioxane; ethyl acetate;

upstream raw materials:

3-azaspiro[5.5]undecane-3-carboxylic acid, 9-oxo, phenylmethyl ester

methyl iodide

Downstream raw materials:

ethyl 2-(3-(2-chloro-5-(trifluoromethoxy)phenyl)-8-methyl-3-azaspiro[5.5]undecan-9-yl)acetate

2-(3-(2-chloro-5-(trifluoromethoxy)phenyl)-8-methyl-3-azaspiro[5.5]undecan-9-yl)acetic acid

Refernces

• 1、 -. "SUBSTITUTED SPIROPIPERIDINYL COMPOUNDS USEFUL AS GPR120 AGONISTS". Page/Page column 61. . Retrieved 2014/05/07.