Tert-butyl 3-(2-ethoxy-2-oxoethylidene)-8-azabicyclo[3.2.1]octane-8-carboxylate

Base Information

• Chemical Name: Tert-butyl 3-(2-ethoxy-2-oxoethylidene)-8-azabicyclo[3.2.1]octane-8-carboxylate
• CAS No.: 865106-60-1
• Molecular Formula: C₁₆H₂₅NO₄
• Molecular Weight: 295.379
• Mol file: 865106-60-1.mol

Synonyms:865106-60-1;tert-butyl 3-(2-ethoxy-2-oxoethylidene)-8-azabicyclo[3.2.1]octane-8-carboxylate;tert-butyl 3-ethoxycarbonylmethylene-8-aza-bicyclo[3.2.1]octane-8-carboxylate;SCHEMBL4087723;GEMJVWXRPBJSJH-UHFFFAOYSA-N;AS-73680;CS-0456622;8-Boc-3-ethoxycarbonylmethylene-8-aza-bicyclo[3.2.1]octane;3-ethoxycarbonylmethylene-8-azabicyclo[3.2.1]octane-8-carb oxylic acid tert-butyl ester;3-Ethoxycarbonylmethylene-8-azabicyclo[3.2.1]octane-8-carboxylic acid t-butyl ester;3-ethoxycarbonylmethylene-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester;tert-butyl 3-ethoxycarbonylmethylene-8-azabicyclo[3.2.1]octane-8-carboxylate

Chemical Property of Tert-butyl 3-(2-ethoxy-2-oxoethylidene)-8-azabicyclo[3.2.1]octane-8-carboxylate

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 295.17835828
• Heavy Atom Count: 21
• Complexity: 434

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C=C1CC2CCC(C1)N2C(=O)OC(C)(C)C

Technology Process of Tert-butyl 3-(2-ethoxy-2-oxoethylidene)-8-azabicyclo[3.2.1]octane-8-carboxylate

There total 1 articles about Tert-butyl 3-(2-ethoxy-2-oxoethylidene)-8-azabicyclo[3.2.1]octane-8-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: 82.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + Boc-tropinone (185099-67-6) → tert-butyl 3-(2-ethoxy-2-oxoethylidene)-8-azabicyclo[3.2.1]octane-8-carboxylate (865106-60-1)

Guidance literature:

With NaH; In tetrahydrofuran;

Reference yield:

tert-butyl 3-(2-ethoxy-2-oxoethylidene)-8-azabicyclo[3.2.1]octane-8-carboxylate (865106-60-1) → tert-butyl 3-(2-{[(4-methylphenyl)sulfonyl]oxy}ethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate

Guidance literature:

Multi-step reaction with 3 steps

1: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 20 °C / 2280.15 Torr

2: diisobutylaluminium hydride / tetrahydrofuran; toluene / 1.5 h / -78 - 0 °C / Inert atmosphere

3: triethylamine / dichloromethane / 20 °C

With palladium 10% on activated carbon; hydrogen; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; toluene;

Reference yield:

tert-butyl 3-(2-ethoxy-2-oxoethylidene)-8-azabicyclo[3.2.1]octane-8-carboxylate (865106-60-1) → ethyl 2-(8-benzyl-8-azabicyclo[3.2.1]octan-3-ylidene)acetate (79521-85-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic acid / dichloromethane / 20 °C

1.2: pH 13

2.1: triethylamine / tetrahydrofuran / 2 h / 20 °C

With triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

Boc-tropinone

Downstream raw materials:

3-{2-[(2-Iodo-phenyl)-(2,2,2-trifluoro-acetyl)-amino]-ethylidene}-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

ethyl 2-(8-benzyl-8-azabicyclo[3.2.1]octan-3-ylidene)acetate

2-(8-benzyl-8-azabicyclo[3.2.1]octan-3-ylidene)-N-hydroxyacetamide