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

Base Information

Chemical Name: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
CAS No.:1307795-88-5
Molecular Formula:C₃₅H₃₈F₂N₂O₅
Molecular Weight:604.694
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 11 articles about 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 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:

: 1307795-83-0
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

: 79-03-8
propionyl chloride

: 1307795-88-5
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

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 20 ℃; for 1.5h;

Reference yield:

: 79099-07-3
N-tert-butyloxycarbonylpiperidin-4-one

: 1307795-88-5
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

Guidance literature:: Multi-step reaction with 8 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

8.1: triethylamine / dichloromethane / 1.5 h / 0 - 20 °C

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)-5,6-difluoro-3'-(4-hydroxy-2-methylphenyl)-3-oxo-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate

: 1307795-88-5
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

Guidance literature:: Multi-step reaction with 4 steps

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

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

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

4: triethylamine / dichloromethane / 1.5 h / 0 - 20 °C

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