(6R,8R)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoquinoline-2-carbaldehyde

Base Information

• Chemical Name: (6R,8R)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoquinoline-2-carbaldehyde
• CAS No.: 888410-75-1
• Molecular Formula: C₁₃H₁₅NO
• Molecular Weight: 201.268
• Mol file: 888410-75-1.mol

Synonyms:(6R,8R)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoquinoline-2-carbaldehyde

Chemical Property of (6R,8R)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoquinoline-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,8R)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoquinoline-2-carbaldehyde

There total 1 articles about (6R,8R)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoquinoline-2-carbaldehyde 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:

(1R,5S)-(+)-nopinone (38651-65-9) → (6R,8R)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoquinoline-2-carbaldehyde (888410-75-1)

Guidance literature:

Multi-step reaction with 4 steps

1: ammonia / methanol / 15 h / 140 °C / 9000.9 Torr / Autoclave; Inert atmosphere

2: triethylamine / dichloromethane / 1.5 h / -78 °C / Inert atmosphere

3: triethylamine; palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene / methanol; N,N-dimethyl-formamide / 24 h / 80 °C / Schlenk technique; Inert atmosphere

4: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -78 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; ammonia; palladium diacetate; diisobutylaluminium hydride; triethylamine; In methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2013.03.004

Reference yield: 95.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (6R,8R)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoquinoline-2-carbaldehyde (888410-75-1) + 4-methoxy-aniline (104-94-9) → (7R,9R)-2-(4-methoxyphenyl)-8,8-dimethyl-6,7,8,9-tetrahydro-7,9-methanoimidazo[1,5-a]quinolin-2-ium chloride (1431378-08-3)

Guidance literature:

With hydrogenchloride; In ethanol; at 20 ℃; for 1h;

DOI:10.1016/j.tetasy.2013.03.004

Reference yield: 93.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (6R,8R)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoquinoline-2-carbaldehyde (888410-75-1) + aniline (62-53-3) → (7R,9R)-8,8-dimethyl-2-phenyl-6,7,8,9-tetrahydro-7,9-methanoimidazo[1,5-a]quinolin-2-ium chloride (1431378-05-0)

Guidance literature:

With hydrogenchloride; In ethanol; at 20 ℃; for 3h;

DOI:10.1016/j.tetasy.2013.03.004

upstream raw materials:

(1R,5S)-(+)-nopinone

Downstream raw materials:

C₂₄H₃₃N₃

C₂₁H₂₇N₃

(7R,9R)-8,8-dimethyl-2-phenyl-6,7,8,9-tetrahydro-7,9-methanoimidazo[1,5-a]quinolin-2-ium chloride

(7R,9R)-2-mesityl-8,8-dimethyl-6,7,8,9-tetrahydro-7,9-methanoimidazo[1,5-a]quinolin-2-ium chloride