3-Boc-3-azaspiro[5.5]undecane-9-carbaldehyde

Base Information

• Chemical Name: 3-Boc-3-azaspiro[5.5]undecane-9-carbaldehyde
• CAS No.: 1416176-14-1
• Molecular Formula: C₁₆H₂₇NO₃
• Molecular Weight: 281.395
• Mol file: 1416176-14-1.mol

Synonyms:3-Boc-3-azaspiro[5.5]undecane-9-carbaldehyde;tert-butyl 9-formyl-3-azaspiro[5.5]undecane-3-carboxylate

Chemical Property of 3-Boc-3-azaspiro[5.5]undecane-9-carbaldehyde

Chemical Property:

• PSA: 46.61000
• LogP: 3.33070

Purity/Quality:

98%,99%, ^*data from raw suppliers

tert-butyl9-formyl-3-azaspiro[5.5]undecane-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Boc-3-azaspiro[5.5]undecane-9-carbaldehyde

There total 2 articles about 3-Boc-3-azaspiro[5.5]undecane-9-carbaldehyde 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:

tert-butyl 9-(methoxymethylidene)-3-azaspiro[5.5]undecane-3-carboxylate (1416176-13-0) → tert-butyl 9-formyl-3-azaspiro[5.5]undecane-3-carboxylate (1416176-14-1)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃;

Reference yield:

9-oxo-3-azaspiro[5.5]undecane-3-carboxylic acid tert-butyl ester (873924-08-4) → tert-butyl 9-formyl-3-azaspiro[5.5]undecane-3-carboxylate (1416176-14-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C

1.2: 1 h

2.1: water; hydrogenchloride / tetrahydrofuran / 20 °C

With hydrogenchloride; potassium tert-butylate; water; In tetrahydrofuran;

Reference yield:

tert-butyl 9-formyl-3-azaspiro[5.5]undecane-3-carboxylate (1416176-14-1) → C20H25ClF3NO3 (1599478-66-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / mineral oil; tetrahydrofuran / 0.17 h / 20 °C

1.2: 1 h / 0 °C / Cooling with ice

2.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 3 h

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

4.1: potassium carbonate / water

5.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 16 h / Inert atmosphere; Heating

6.1: lithium hydroxide monohydrate / water; tetrahydrofuran / 24 h

With hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; lithium hydroxide monohydrate; palladium 10% on activated carbon; hydrogen; sodium hydride; potassium carbonate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In tetrahydrofuran; 1,4-dioxane; water; ethyl acetate; mineral oil; 1.1: |Horner-Wadsworth-Emmons Olefination / 1.2: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1021/acsmedchemlett.6b00360

upstream raw materials:

9-oxo-3-azaspiro[5.5]undecane-3-carboxylic acid tert-butyl ester

tert-butyl 9-(methoxymethylidene)-3-azaspiro[5.5]undecane-3-carboxylate

Downstream raw materials:

3-(3-(5-cyclobutoxy-2-fluorophenyl)-3-azaspiro[5.5]undecan-9-yl)propanoic acid

ethyl 3-(3-(5-cyclobutoxy-2-fluorophenyl)-3-azaspiro[5.5]undecan-9-yl)propanoate

C₂₀H₂₅ClF₃NO₃

tert-butyl 9-{3-[4-(methanesulfonyl)phenoxy]propyl}-3-azaspiro[5.5]undecane-3-carboxylate

Refernces

• 1、 Cox, Jason M.,Chu, Hong D.,Chelliah, Mariappan V.,Debenham, John S.,Eagen, Keith,Lan, Ping,Lombardo, Matthew,London, Clare,Plotkin, Michael A.,Shah, Unmesh,Sun, Zhongxiang,Vaccaro, Henry M.,Venkatraman, Srikanth,Suzuki, Takao,Wang, Nengxue,Ashley, Eric R.,Crespo, Alejandro,Madeira, Maria,Leung, Dennis H.,Alleyne, Candice,Ogawa, Aimie M.,Souza, Sarah,Thomas-Fowlkes, Brande,Di Salvo, Jerry,Weinglass, Adam,Kirkland, Melissa,Pachanski, Michele,Powles, Mary Ann,Tozzo, Effie,Akiyama, Taro E.,Ujjainwalla, Feroze,Tata, James R.,Sinz, Christopher J.. "Design, synthesis, and evaluation of novel and selective G-protein coupled receptor 120 (GPR120) spirocyclic agonists". . p. 49 - 54. Retrieved 2017/12/12.