(6S,9R)-6-(3,5-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one

Base Information

• Chemical Name: (6S,9R)-6-(3,5-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one
• CAS No.: 1289024-27-6
• Molecular Formula: C₂₅H₃₃F₂NO₂Si
• Molecular Weight: 445.625
• Mol file: 1289024-27-6.mol

Synonyms:(6S,9R)-6-(3,5-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one

Chemical Property of (6S,9R)-6-(3,5-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S,9R)-6-(3,5-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one

There total 1 articles about (6S,9R)-6-(3,5-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one 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: 51.0%

3,5-difluorobromobenzene (461-96-1) + (R)-9-((triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one (1190363-45-1) → (6S,9R)-6-(3,5-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one (1289024-27-6)

Guidance literature:

With palladium diacetate; sodium t-butanolate; 2-(dicyclohexylphosphino)-2'-methylbiphenyl; In toluene; at 80 ℃; for 18h; Inert atmosphere;

Reference yield: 56.0%

(6S,9R)-6-(3,5-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one (1289024-27-6) → (5S,6S,9R)-6-(3,5-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ol (1289024-25-4)

Guidance literature:

(6S,9R)-6-(3,5-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one; With lithium borohydride; In cyclopentyl methyl ether; at 0 - 20 ℃; for 6h; Inert atmosphere;

With methanol; In cyclopentyl methyl ether; for 0.5h;

Reference yield:

(6S,9R)-6-(3,5-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one (1289024-27-6) → (5S,6S,9R)-6-(3,5-difluorophenyl)-5-hydroxy-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate (1289023-70-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium borohydride / cyclopentyl methyl ether / 6 h / 0 - 20 °C / Inert atmosphere

1.2: 0.5 h

2.1: dmap; triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

4.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / 4 h / -20 - -10 °C / Inert atmosphere

4.2: 1 h / 20 °C

With dmap; lithium borohydride; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; triethylamine; In tetrahydrofuran; dichloromethane; cyclopentyl methyl ether; N,N-dimethyl-formamide;

upstream raw materials:

3,5-difluorobromobenzene

(R)-9-((triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one

Downstream raw materials:

(5S,6S,9R)-6-(3,5-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ol

(5S,6S,9R)-5-amino-6-(3,5-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate

(5S,6S,9R)-5-azido-6-(3,5-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine

(5S,6S,9R)-5-azido-6-(3,5-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-ol