(1R,4S,6R)-2-Aza-bicyclo[2.2.2]octane-6-carboxylic acid [(R)-2-(4-tert-butylcarbamoyl-4-cyclohexyl-piperidin-1-yl)-1-(4-fluoro-benzyl)-2-oxo-ethyl]-amide

Base Information

• Chemical Name: (1R,4S,6R)-2-Aza-bicyclo[2.2.2]octane-6-carboxylic acid [(R)-2-(4-tert-butylcarbamoyl-4-cyclohexyl-piperidin-1-yl)-1-(4-fluoro-benzyl)-2-oxo-ethyl]-amide
• CAS No.: 491845-97-7
• Molecular Formula: C₃₃H₄₉FN₄O₃
• Molecular Weight: 568.775

Synonyms:

Chemical Property of (1R,4S,6R)-2-Aza-bicyclo[2.2.2]octane-6-carboxylic acid [(R)-2-(4-tert-butylcarbamoyl-4-cyclohexyl-piperidin-1-yl)-1-(4-fluoro-benzyl)-2-oxo-ethyl]-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S,6R)-2-Aza-bicyclo[2.2.2]octane-6-carboxylic acid [(R)-2-(4-tert-butylcarbamoyl-4-cyclohexyl-piperidin-1-yl)-1-(4-fluoro-benzyl)-2-oxo-ethyl]-amide

There total 12 articles about (1R,4S,6R)-2-Aza-bicyclo[2.2.2]octane-6-carboxylic acid [(R)-2-(4-tert-butylcarbamoyl-4-cyclohexyl-piperidin-1-yl)-1-(4-fluoro-benzyl)-2-oxo-ethyl]-amide 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:

2-benzyl 7-methyl 2-azabicyclo[2.2.2]oct-5-ene-2,7-dicarboxylate → (1R,4S,6R)-2-Aza-bicyclo[2.2.2]octane-6-carboxylic acid [(R)-2-(4-tert-butylcarbamoyl-4-cyclohexyl-piperidin-1-yl)-1-(4-fluoro-benzyl)-2-oxo-ethyl]-amide (491845-97-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: aq. NaOH / methanol

1.2: iodine; KI; aq. NaHCO₃ / methanol

2.1: zinc; acetic acid

3.1: H₂ / Pd/C / methanol

4.1: NaOH / dioxane

5.1: pivaloyl chloride; LiCl; Et₃N / tetrahydrofuran

6.1: aq. LiOH; H₂O₂ / tetrahydrofuran

7.1: EDC; HOBt; DIEA / CH₂Cl₂

8.1: HCl / dioxane

With hydrogenchloride; lithium hydroxide; sodium hydroxide; hydrogen; dihydrogen peroxide; pivaloyl chloride; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; zinc; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1016/j.bmcl.2005.05.109

Reference yield:

(1R,4R,6R)-2-Aza-bicyclo[2.2.2]oct-7-ene-2,6-dicarboxylic acid 2-benzyl ester → (1R,4S,6R)-2-Aza-bicyclo[2.2.2]octane-6-carboxylic acid [(R)-2-(4-tert-butylcarbamoyl-4-cyclohexyl-piperidin-1-yl)-1-(4-fluoro-benzyl)-2-oxo-ethyl]-amide (491845-97-7)

Guidance literature:

Multi-step reaction with 6 steps

1: H₂ / Pd/C / methanol

2: NaOH / dioxane

3: pivaloyl chloride; LiCl; Et₃N / tetrahydrofuran

4: aq. LiOH; H₂O₂ / tetrahydrofuran

5: EDC; HOBt; DIEA / CH₂Cl₂

6: HCl / dioxane

With hydrogenchloride; lithium hydroxide; sodium hydroxide; hydrogen; dihydrogen peroxide; pivaloyl chloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1016/j.bmcl.2005.05.109

Reference yield:

8-(benzyloxycarbonyl)-2-iodo-4-oxa-8-azatricyclo[4.3.1.03,7]decan-5-one → (1R,4S,6R)-2-Aza-bicyclo[2.2.2]octane-6-carboxylic acid [(R)-2-(4-tert-butylcarbamoyl-4-cyclohexyl-piperidin-1-yl)-1-(4-fluoro-benzyl)-2-oxo-ethyl]-amide (491845-97-7)

Guidance literature:

Multi-step reaction with 7 steps

1: zinc; acetic acid

2: H₂ / Pd/C / methanol

3: NaOH / dioxane

4: pivaloyl chloride; LiCl; Et₃N / tetrahydrofuran

5: aq. LiOH; H₂O₂ / tetrahydrofuran

6: EDC; HOBt; DIEA / CH₂Cl₂

7: HCl / dioxane

With hydrogenchloride; lithium hydroxide; sodium hydroxide; hydrogen; dihydrogen peroxide; pivaloyl chloride; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; zinc; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1016/j.bmcl.2005.05.109

upstream raw materials:

(1R,4S,6R)-2-Aza-bicyclo[2.2.2]octane-2,6-dicarboxylic acid 2-tert-butyl ester

N-benzyloxycarbonyl-1,2-dihydropyridine

N-(tert-butyl)-4-cyclohexylpiperidine-4-carboxamide

1-[(2R)-2-amino-3-(4-fluorophenyl)-1-oxopropyl]-4-cyclohexyl-N-(1,1-dimethylethyl)-4-piperidine carboxamide

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