(1S,4R,6S)-6-[(R)-2-(4-tert-Butylcarbamoyl-4-cyclohexyl-piperidin-1-yl)-1-(4-fluoro-benzyl)-2-oxo-ethylcarbamoyl]-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (1S,4R,6S)-6-[(R)-2-(4-tert-Butylcarbamoyl-4-cyclohexyl-piperidin-1-yl)-1-(4-fluoro-benzyl)-2-oxo-ethylcarbamoyl]-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester
• CAS No.: 491845-84-2
• Molecular Formula: C₃₈H₅₇FN₄O₅
• Molecular Weight: 668.893

Synonyms:

Chemical Property of (1S,4R,6S)-6-[(R)-2-(4-tert-Butylcarbamoyl-4-cyclohexyl-piperidin-1-yl)-1-(4-fluoro-benzyl)-2-oxo-ethylcarbamoyl]-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R,6S)-6-[(R)-2-(4-tert-Butylcarbamoyl-4-cyclohexyl-piperidin-1-yl)-1-(4-fluoro-benzyl)-2-oxo-ethylcarbamoyl]-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester

There total 13 articles about (1S,4R,6S)-6-[(R)-2-(4-tert-Butylcarbamoyl-4-cyclohexyl-piperidin-1-yl)-1-(4-fluoro-benzyl)-2-oxo-ethylcarbamoyl]-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid tert-butyl 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:

2-benzyl 7-methyl 2-azabicyclo[2.2.2]oct-5-ene-2,7-dicarboxylate → (1S,4R,6S)-6-[(R)-2-(4-tert-Butylcarbamoyl-4-cyclohexyl-piperidin-1-yl)-1-(4-fluoro-benzyl)-2-oxo-ethylcarbamoyl]-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester (491845-84-2)

Guidance literature:

Multi-step reaction with 7 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

With 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 → (1S,4R,6S)-6-[(R)-2-(4-tert-Butylcarbamoyl-4-cyclohexyl-piperidin-1-yl)-1-(4-fluoro-benzyl)-2-oxo-ethylcarbamoyl]-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester (491845-84-2)

Guidance literature:

Multi-step reaction with 5 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

With 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 → (1S,4R,6S)-6-[(R)-2-(4-tert-Butylcarbamoyl-4-cyclohexyl-piperidin-1-yl)-1-(4-fluoro-benzyl)-2-oxo-ethylcarbamoyl]-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester (491845-84-2)

Guidance literature:

Multi-step reaction with 6 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

With 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:

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

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

pyridine

di-tert-butyl dicarbonate

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