(4aS,9aS)-5-methoxy-4a-(3-methoxyphenyl)-4,4a,9,9a-tetrahydro-1H-indeno[2,1-b]-pyridin-3(2H)-one

Base Information

• Chemical Name: (4aS,9aS)-5-methoxy-4a-(3-methoxyphenyl)-4,4a,9,9a-tetrahydro-1H-indeno[2,1-b]-pyridin-3(2H)-one
• CAS No.: 1045814-84-3
• Molecular Formula: C₂₀H₂₁NO₃
• Molecular Weight: 323.392
• Mol file: 1045814-84-3.mol

Synonyms:(4aS,9aS)-5-methoxy-4a-(3-methoxyphenyl)-4,4a,9,9a-tetrahydro-1H-indeno[2,1-b]-pyridin-3(2H)-one

Chemical Property of (4aS,9aS)-5-methoxy-4a-(3-methoxyphenyl)-4,4a,9,9a-tetrahydro-1H-indeno[2,1-b]-pyridin-3(2H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aS,9aS)-5-methoxy-4a-(3-methoxyphenyl)-4,4a,9,9a-tetrahydro-1H-indeno[2,1-b]-pyridin-3(2H)-one

There total 3 articles about (4aS,9aS)-5-methoxy-4a-(3-methoxyphenyl)-4,4a,9,9a-tetrahydro-1H-indeno[2,1-b]-pyridin-3(2H)-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: 94.0%

(4aS,9aS)-benzyl-5-methoxy-4a-(3-methoxyphenyl)-3-oxo-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine-1-carboxylate (1045814-79-6) → (4aS,9aS)-5-methoxy-4a-(3-methoxyphenyl)-4,4a,9,9a-tetrahydro-1H-indeno[2,1-b]-pyridin-3(2H)-one (1045814-84-3)

Guidance literature:

With 10% Pd/C; hydrogen; In methanol; for 0.333333h; under 760.051 Torr;

DOI:10.1039/b805295f

Reference yield: 87.0%

benzyl (4aS,9aS)-8-bromo-5-methoxy-4a-(3-methoxyphenyl)-3-oxo-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine-1-carboxylate (1300035-45-3) → (4aS,9aS)-5-methoxy-4a-(3-methoxyphenyl)-4,4a,9,9a-tetrahydro-1H-indeno[2,1-b]-pyridin-3(2H)-one (1045814-84-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; triethylamine; In methanol; at 20 ℃; for 1h; under 760.051 Torr;

DOI:10.1021/ol200725m

Reference yield:

benzyl (4aS,9aS)-8-bromo-3-hydroxy-5-methoxy-4a-(3-methoxyphenyl)-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine-1-carboxylate → (4aS,9aS)-5-methoxy-4a-(3-methoxyphenyl)-4,4a,9,9a-tetrahydro-1H-indeno[2,1-b]-pyridin-3(2H)-one (1045814-84-3)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 2.5 h / -78 - 20 °C / Inert atmosphere

2: palladium 10% on activated carbon; hydrogen; triethylamine / methanol / 1 h / 20 °C / 760.05 Torr

With oxalyl dichloride; palladium 10% on activated carbon; hydrogen; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; 1: Swern oxidation;

DOI:10.1021/ol200725m

upstream raw materials:

(4aS,9aS)-benzyl-5-methoxy-4a-(3-methoxyphenyl)-3-oxo-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine-1-carboxylate

benzyl (4aS,9aS)-8-bromo-5-methoxy-4a-(3-methoxyphenyl)-3-oxo-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine-1-carboxylate

Downstream raw materials:

(4aS,9aS)-5-methoxy-4a-(3-methoxyphenyl)-1-(4-(tri-iso-propylsilyl)but-3-ynyl)-4,4a,9,9a-tetrahydro-1H-indeno[2,1-b]pyridin-3(2H)-one