(3aR^*,6R^*,7aS^*)-6-(benzyloxy)octahydro-3a-(3,4-dimethoxyphenyl)-1-methylindol-2-one

Base Information

• Chemical Name: (3aR^*,6R^*,7aS^*)-6-(benzyloxy)octahydro-3a-(3,4-dimethoxyphenyl)-1-methylindol-2-one
• CAS No.: 82732-18-1
• Molecular Formula: C₂₄H₂₉NO₄
• Molecular Weight: 395.499
• Mol file: 82732-18-1.mol

Synonyms:(3aR^*,6R^*,7aS^*)-6-(benzyloxy)octahydro-3a-(3,4-dimethoxyphenyl)-1-methylindol-2-one

Chemical Property of (3aR^*,6R^*,7aS^*)-6-(benzyloxy)octahydro-3a-(3,4-dimethoxyphenyl)-1-methylindol-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR^*,6R^*,7aS^*)-6-(benzyloxy)octahydro-3a-(3,4-dimethoxyphenyl)-1-methylindol-2-one

There total 16 articles about (3aR^*,6R^*,7aS^*)-6-(benzyloxy)octahydro-3a-(3,4-dimethoxyphenyl)-1-methylindol-2-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: 26.0%

(1S*,5R*)-N-<5-(benzyloxy)-2-(3,4-dimethoxyphenyl)cyclohex-2-en-1-yl>-α,α-dichloro-N-methylacetamide (125032-08-8) → (3aR*,6R*,7aS*)-6-(benzyloxy)octahydro-3a-(3,4-dimethoxyphenyl)-1-methylindol-2-one (82732-18-1) + (1S*,5R*)-N-<5-(benzyloxy)-2-(3,4-dimethoxyphenyl)cyclohex-2-en-1-yl>-N-methylacetamide (125032-10-2)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; Heating;

DOI:10.1021/jo00001a021

Reference yield:

4-(benzyloxy)-1-(3,4-dimethoxyphenyl)cyclohex-1-ene (82732-16-9) → (3aR*,6R*,7aS*)-6-(benzyloxy)octahydro-3a-(3,4-dimethoxyphenyl)-1-methylindol-2-one (82732-18-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 10 percent / N-bromosuccinimide / acetonitrile; H₂O

2: 83 percent / methanol / 100 °C / in a sealed tube

3: 8 percent / NEt₃ / CH₂Cl₂

4: 51 percent / Bu₃SnH, AIBN / toluene / Heating

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethylamine; In methanol; dichloromethane; water; toluene; acetonitrile;

DOI:10.1039/c39890000762

Reference yield:

(1R*,2S*,4R*)-4-(benzyloxy)-1-(3,4-dimethoxyphenyl)-2-(methylamino)cyclohexan-1-ol (125032-06-6) → (3aR*,6R*,7aS*)-6-(benzyloxy)octahydro-3a-(3,4-dimethoxyphenyl)-1-methylindol-2-one (82732-18-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 8 percent / NEt₃ / CH₂Cl₂

2: 51 percent / Bu₃SnH, AIBN / toluene / Heating

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethylamine; In dichloromethane; toluene;

DOI:10.1039/c39890000762

upstream raw materials:

(1S^*,5R^*)-N-<5-(benzyloxy)-2-(3,4-dimethoxyphenyl)cyclohex-2-en-1-yl>-α,α-dichloro-N-methylacetamide

4-(benzyloxy)-1-(3,4-dimethoxyphenyl)cyclohex-1-ene

(1R^*,2S^*,4R^*)-4-(benzyloxy)-1-(3,4-dimethoxyphenyl)-2-(methylamino)cyclohexan-1-ol

(1S^*,2R^*,5R^*)-N-<5-(benzyloxy)-2-hydroxy-2-(3,4-dimethoxyphenyl)cyclohex-1-yl>-α,α-dichloro-N-methylacetamide

Downstream raw materials:

(+/-)-mesembranol

1-methyl-3a-(3,4-dimethoxyphenyl)-6-(benzyloxy)-cis-octahydroindole

(3aR,7aR)-3a-(3,4-Dimethoxy-phenyl)-6-hydroxy-1-methyl-octahydro-indol-2-one

(3aR^*,6R^*,7aS^*)-6-(benzyloxy)octahydro-3a-(3,4-dimethoxyphenyl)-1-methylindole