(1S,3R,4aS,7R,8aR)-10-benzyl-3-methyloctahydro-1,7-(epiminomethano)naphthalen-6(2H)-one

Base Information

• Chemical Name: (1S,3R,4aS,7R,8aR)-10-benzyl-3-methyloctahydro-1,7-(epiminomethano)naphthalen-6(2H)-one
• CAS No.: 1448722-42-6
• Molecular Formula: C₁₉H₂₅NO
• Molecular Weight: 283.414
• Mol file: 1448722-42-6.mol

Synonyms:(1S,3R,4aS,7R,8aR)-10-benzyl-3-methyloctahydro-1,7-(epiminomethano)naphthalen-6(2H)-one

Chemical Property of (1S,3R,4aS,7R,8aR)-10-benzyl-3-methyloctahydro-1,7-(epiminomethano)naphthalen-6(2H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,4aS,7R,8aR)-10-benzyl-3-methyloctahydro-1,7-(epiminomethano)naphthalen-6(2H)-one

There total 1 articles about (1S,3R,4aS,7R,8aR)-10-benzyl-3-methyloctahydro-1,7-(epiminomethano)naphthalen-6(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: 74.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (3R,4aS,8aR)-N-benzyl-6-(tert-butyldimethylsilyloxy)-3-methyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-amine → (1S,3R,4aS,7R,8aR)-10-benzyl-3-methyloctahydro-1,7-(epiminomethano)naphthalen-6(2H)-one (1448722-42-6)

Guidance literature:

In ethanol; water; at 20 ℃; for 48h;

DOI:10.1021/ol401954f

Reference yield:

(1S,3R,4aS,7R,8aR)-10-benzyl-3-methyloctahydro-1,7-(epiminomethano)naphthalen-6(2H)-one (1448722-42-6) → (5S,6aR,7S,9R,10aS)-benzyl 9-methyl-2-oxo-2,5,6,6a,7,8,9,10,10a,11-decahydro-1H-7,5-(epiminomethano)benzo[5,6]cyclohepta[1,2-b]pyridine-12-carboxylate (1448722-48-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol / 22 h / 20 °C / Inert atmosphere

2.1: potassium carbonate / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

3.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 5.08 h / -78 °C / Inert atmosphere

4.1: rhodium(II) acetate dimer / dichloromethane / 2.5 h / 20 °C / Inert atmosphere

5.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C / Inert atmosphere

5.2: 24.5 h / 0 - 20 °C / Inert atmosphere

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride / tetrahydrofuran / 15 h / 20 - 50 °C / Inert atmosphere

7.1: sodium hydroxide; ethanol / 13.5 h / 60 °C / Inert atmosphere

8.1: triethylamine; diphenyl phosphoryl azide / toluene / 12 h / 20 °C / Inert atmosphere

9.1: toluene / 3 h / 80 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; rhodium(II) acetate dimer; ethanol; diphenyl phosphoryl azide; 10 wt% Pd(OH)2 on carbon; hydrogen; sodium hydride; potassium carbonate; triethylamine; lithium chloride; sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; mineral oil; 6.1: |Stille Cross Coupling;

DOI:10.1021/ol401954f

Reference yield:

(1S,3R,4aS,7R,8aR)-10-benzyl-3-methyloctahydro-1,7-(epiminomethano)naphthalen-6(2H)-one (1448722-42-6) → C24H31NO5 (1448722-39-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol / 22 h / 20 °C / Inert atmosphere

2: potassium carbonate / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

3: lithium diisopropyl amide / hexane; tetrahydrofuran / 5.08 h / -78 °C / Inert atmosphere

4: rhodium(II) acetate dimer / dichloromethane / 2.5 h / 20 °C / Inert atmosphere

With rhodium(II) acetate dimer; 10 wt% Pd(OH)2 on carbon; hydrogen; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1021/ol401954f

upstream raw materials:

formaldehyd

Downstream raw materials:

(1S,3R,4aS,8S,9aR)-11-benzyl 6-ethyl 3-methyl-7-vinyl-2,3,4,4a,5,8,9,9a-octahydro-1H-1,8-(epiminomethano)benzo[7]annulene-6,11-dicarboxylate

(1S,3R,4aS,8S,9aR)-11-((benzyloxy)carbonyl)-3-methyl-7-vinyl-2,3,4,4a,5,8,9,9a-octahydro-1H-1,8-(epiminomethano)benzo[7]annulene-6-carboxylic acid

(5S,6aR,7S,9R,10aS)-benzyl 9-methyl-2-oxo-2,5,6,6a,7,8,9,10,10a,11-decahydro-1H-7,5-(epiminomethano)benzo[5,6]cyclohepta[1,2-b]pyridine-12-carboxylate

C₂₄H₃₁NO₅