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

Base Information

• Chemical Name: (3aR^*,6R^*,7aS^*)-6-(benzyloxy)octahydro-3a-(3,4-dimethoxyphenyl)-1-methylindole
• CAS No.: 82732-19-2
• Molecular Formula: C₂₄H₃₁NO₃
• Molecular Weight: 381.515

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (3aR^*,6R^*,7aS^*)-6-(benzyloxy)octahydro-3a-(3,4-dimethoxyphenyl)-1-methylindole

There total 20 articles about (3aR^*,6R^*,7aS^*)-6-(benzyloxy)octahydro-3a-(3,4-dimethoxyphenyl)-1-methylindole 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: 81.0%

(3aR*,6R*,7aS*)-6-(benzyloxy)octahydro-3a-(3,4-dimethoxyphenyl)-1-methylindol-2-one (82732-18-1) → (3aR*,6R*,7aS*)-6-(benzyloxy)octahydro-3a-(3,4-dimethoxyphenyl)-1-methylindole (82732-19-2)

Guidance literature:

With borane-THF; In tetrahydrofuran; for 1h; Heating;

DOI:10.1021/jo00001a021

Reference yield: 74.5%

1-methyl-3a-(3,4-dimethoxyphenyl)-6-(benzyloxy)-cis-octahydroindol-2-one (82732-18-1,82732-27-2) → 1-methyl-3a-(3,4-dimethoxyphenyl)-6-(benzyloxy)-cis-octahydroindole (82732-19-2,82732-28-3)

Guidance literature:

With borane-THF; In tetrahydrofuran; for 1h; Heating;

DOI:10.1021/jo00141a015

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-methylindole (82732-19-2)

Guidance literature:

Multi-step reaction with 5 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

5: 81 percent / BH₃ / tetrahydrofuran / 0 deg C, than reflux

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

DOI:10.1039/c39890000762

upstream raw materials:

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

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

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

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

Downstream raw materials:

(+/-)-mesembranol

(+/-)-6-epimesembranol

mesembrine

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