tert-butyl (5S,6S)-6-(2,3-difluorophenyl)-9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate

Base Information

• Chemical Name: tert-butyl (5S,6S)-6-(2,3-difluorophenyl)-9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate
• CAS No.: 1289024-65-2
• Molecular Formula: C₂₁H₂₂F₂N₂O₃
• Molecular Weight: 388.414
• Mol file: 1289024-65-2.mol

Synonyms:tert-butyl (5S,6S)-6-(2,3-difluorophenyl)-9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate

Chemical Property of tert-butyl (5S,6S)-6-(2,3-difluorophenyl)-9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (5S,6S)-6-(2,3-difluorophenyl)-9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate

There total 6 articles about tert-butyl (5S,6S)-6-(2,3-difluorophenyl)-9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate 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: 73.0%

tert-butyl (5S,6S,9R)-6-(2,3-difluorophenyl)-9-hydroxy-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate (1289024-48-1) → tert-butyl (5S,6S)-6-(2,3-difluorophenyl)-9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate (1289024-65-2)

Guidance literature:

tert-butyl (5S,6S,9R)-6-(2,3-difluorophenyl)-9-hydroxy-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -65 ℃; for 2h;

With triethylamine; In dichloromethane; at -65 - 20 ℃;

Reference yield:

(5S,6S,9R)-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]-pyridin-5-ol (1190363-50-8) → tert-butyl (5S,6S)-6-(2,3-difluorophenyl)-9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate (1289024-65-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: N-chloro-succinimide; triphenylphosphine / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere

2.1: sodium azide / N,N-dimethyl-formamide / 17.5 h / 20 - 50 °C / Inert atmosphere

3.1: hydrogen / palladium 10% on activated carbon / ethanol / 7.5 h / 760.05 Torr

4.1: tetrahydrofuran / 20 °C

5.1: N-butyl-N,N-dipropylbutan-1-aminium fluoride / tetrahydrofuran / 1 h / 20 °C

6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -65 °C

6.2: -65 - 20 °C

With N-chloro-succinimide; sodium azide; oxalyl dichloride; N-butyl-N,N-dipropylbutan-1-aminium fluoride; hydrogen; dimethyl sulfoxide; triphenylphosphine; palladium 10% on activated carbon; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 6.1: Swern Oxidation / 6.2: Swern Oxidation;

Reference yield:

(5R,6S,9R)-5-chloro-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine (1289024-04-9) → tert-butyl (5S,6S)-6-(2,3-difluorophenyl)-9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate (1289024-65-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium azide / N,N-dimethyl-formamide / 17.5 h / 20 - 50 °C / Inert atmosphere

2.1: hydrogen / palladium 10% on activated carbon / ethanol / 7.5 h / 760.05 Torr

3.1: tetrahydrofuran / 20 °C

4.1: N-butyl-N,N-dipropylbutan-1-aminium fluoride / tetrahydrofuran / 1 h / 20 °C

5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -65 °C

5.2: -65 - 20 °C

With sodium azide; oxalyl dichloride; N-butyl-N,N-dipropylbutan-1-aminium fluoride; hydrogen; dimethyl sulfoxide; palladium 10% on activated carbon; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 5.1: Swern Oxidation / 5.2: Swern Oxidation;

upstream raw materials:

(5S,6S,9R)-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]-pyridin-5-ol

(5S,6S,9R)-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-amine

tert-butyl (5S,6S,9R)-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate

tert-butyl (5S,6S,9R)-6-(2,3-difluorophenyl)-9-hydroxy-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate

Downstream raw materials:

ethyl 2-((5S,6S,9S)-5-(tert-butoxycarbonylamino)-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl)acetate

ethyl 2-((5S,6S,9R)-5-(tert-butoxycarbonylamino)-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl)acetate

2-((5S,6S,9S)-5-(tert-butoxycarbonylamino)-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl)acetic acid

tert-butyl (5S,6S,9S)-6-(2,3-difluorophenyl)-9-(2-oxo-2-(4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidin-1-yl)ethyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate