tert-butyl (1R,3'S)-3'-[2'-(2-aminoethyl)-3-methyl-4-biphenylyl]-5,6-difluoro-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate

Base Information

• Chemical Name: tert-butyl (1R,3'S)-3'-[2'-(2-aminoethyl)-3-methyl-4-biphenylyl]-5,6-difluoro-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate
• CAS No.: 1307795-83-0
• Molecular Formula: C₃₂H₃₄F₂N₂O₄
• Molecular Weight: 548.63
• Mol file: 1307795-83-0.mol

Synonyms:tert-butyl (1R,3'S)-3'-[2'-(2-aminoethyl)-3-methyl-4-biphenylyl]-5,6-difluoro-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate

Chemical Property of tert-butyl (1R,3'S)-3'-[2'-(2-aminoethyl)-3-methyl-4-biphenylyl]-5,6-difluoro-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (1R,3'S)-3'-[2'-(2-aminoethyl)-3-methyl-4-biphenylyl]-5,6-difluoro-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate

There total 10 articles about tert-butyl (1R,3'S)-3'-[2'-(2-aminoethyl)-3-methyl-4-biphenylyl]-5,6-difluoro-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-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:

tert-butyl (1R,3'S)-3'-[2'-(2-{[(benzyloxy)carbonyl]amino}ethyl)-3-methyl-4-biphenylyl]-5,6-difluoro-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate (1307795-80-7) → tert-butyl (1R,3'S)-3'-[2'-(2-aminoethyl)-3-methyl-4-biphenylyl]-5,6-difluoro-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate (1307795-83-0)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In ethanol; at 20 ℃; for 20h; Inert atmosphere;

Reference yield:

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → tert-butyl (1R,3'S)-3'-[2'-(2-aminoethyl)-3-methyl-4-biphenylyl]-5,6-difluoro-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate (1307795-83-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium t-butanolate / tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 1,1'-bis(di-tertbutylphosphino)ferrocene / tetrahydrofuran / 12 h / 70 °C / Inert atmosphere

2.1: 1H-imidazole / dmap / N,N-dimethyl-formamide / 48 h / 20 °C

3.1: n-butyllithium; cerium(III) chloride; dibutylmagnesium / hexane; tetrahydrofuran / 0.67 h / -78 - 0 °C

3.2: 3 h / 20 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

5.1: triethylamine / dichloromethane / 2 h / 0 °C

6.1: potassium phosphate / palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere

7.1: hydrogen / palladium 10% on activated carbon / ethanol / 20 h / 20 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; cerium(III) chloride; dibutylmagnesium; tetrabutyl ammonium fluoride; hydrogen; triethylamine; sodium t-butanolate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 1,1'-bis(di-tertbutylphosphino)ferrocene; palladium 10% on activated carbon; palladium diacetate; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

rac-tert-butyl (1R,3'S)-3'-(4-{[tert-butyl(dimethyl)silyl]oxy})-2-methylphenyl-5,6-difluoro-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate → tert-butyl (1R,3'S)-3'-[2'-(2-aminoethyl)-3-methyl-4-biphenylyl]-5,6-difluoro-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate (1307795-83-0)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

2: triethylamine / dichloromethane / 2 h / 0 °C

3: potassium phosphate / palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere

4: hydrogen / palladium 10% on activated carbon / ethanol / 20 h / 20 °C / Inert atmosphere

With tetrabutyl ammonium fluoride; hydrogen; triethylamine; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium 10% on activated carbon; palladium diacetate; In tetrahydrofuran; ethanol; dichloromethane;

upstream raw materials:

N-tert-butyloxycarbonylpiperidin-4-one

benzyl {2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl}carbamate

N-benzyloxycarbonyl-o-bromophenethylamine

tert-butyl (1R,3'S)-3'-[2'-(2-{[(benzyloxy)carbonyl]amino}ethyl)-3-methyl-4-biphenylyl]-5,6-difluoro-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate

Downstream raw materials:

tert-butyl (1R,3'S)-3'-{2'-[2-(acetylamino)ethyl]-3-methyl-4-biphenylyl}-5,6-difluoro-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate

tert-butyl (1R,3'S)-5,6-difluoro-3'-(2'-{2-[(methoxycarbonyl)amino]ethyl}-3-methyl-4-biphenylyl)-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate

tert-butyl (1R,3'S)-5,6-difluoro-3'-{3-methyl-2'-[2-(propionylamino)ethyl]-4-biphenylyl}-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate

tert-butyl (1R,3'S)-3'-[2'-(2-{[(acetyloxy)acetyl]amino}ethyl)-3-methyl-4-biphenylyl]-5,6-difluoro-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate