(3aR,6S,7aR)-3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-1H-indol-6-ol

Base Information

• Chemical Name: (3aR,6S,7aR)-3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-1H-indol-6-ol
• CAS No.: 1427472-33-0
• Molecular Formula: C₁₇H₂₅NO₃
• Molecular Weight: 291.39

Synonyms:(3aR,6S,7aR)-3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-1H-indol-6-ol

Chemical Property of (3aR,6S,7aR)-3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-1H-indol-6-ol

Chemical Property:

Purity/Quality:

> 95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,6S,7aR)-3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-1H-indol-6-ol

There total 10 articles about (3aR,6S,7aR)-3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-1H-indol-6-ol 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: 57.0%

(3aR,6S,7aR)-benzyl 3a-(3,4-dimethoxyphenyl)-6-hydroxyoctahydro-1H-indole-1-carboxylate (1427435-87-7) → (3aR,6S,7aR)-3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-1H-indol-6-ol (1427472-33-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h; Inert atmosphere; Reflux;

DOI:10.1021/jo4000306

Reference yield:

N-allyl-2-bromo-4,5-dimethoxy-N-((1R,5S)-2-methylene-5-(prop-1-en-2-yl)cyclohexyl)benzene sulfonamide (1427435-78-6) → (3aR,6S,7aR)-3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-1H-indol-6-ol (1427472-33-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 15 h / 40 °C

2.1: palladium diacetate; triphenylphosphine; potassium carbonate / N,N-dimethyl-formamide / 15 h / 110 °C / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 15 h / 20 °C

3.2: 15 h / 0 - 20 °C

4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 19 h / 20 °C / 760.05 Torr

5.1: 3-chloro-benzenecarboperoxoic acid / chloroform-d1; water-d2 / 48 h / 20 °C

6.1: lithium; ammonia / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

6.2: 4 h / 20 °C

7.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Inert atmosphere; Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lithium aluminium tetrahydride; palladium 10% on activated carbon; ammonia; hydrogen; palladium diacetate; lithium; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; chloroform-d1; dichloromethane; water-d2; ethyl acetate; N,N-dimethyl-formamide; 2.1: |Heck Reaction;

DOI:10.1021/jo4000306

Reference yield:

2,2,2-trichloro-N-((5S)-2-methylene-5-(prop-1-en-2-yl)cyclohexyl)acetamide → (3aR,6S,7aR)-3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-1H-indol-6-ol (1427472-33-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium hydroxide / dichloromethane; ethanol; water / 15 h / 50 °C

2.1: triethylamine / dichloromethane / 5 h / 0 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C

3.2: 15 h / 0 - 20 °C

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 15 h / 40 °C

5.1: palladium diacetate; triphenylphosphine; potassium carbonate / N,N-dimethyl-formamide / 15 h / 110 °C / Inert atmosphere

6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 15 h / 20 °C

6.2: 15 h / 0 - 20 °C

7.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 19 h / 20 °C / 760.05 Torr

8.1: 3-chloro-benzenecarboperoxoic acid / chloroform-d1; water-d2 / 48 h / 20 °C

9.1: lithium; ammonia / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

9.2: 4 h / 20 °C

10.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Inert atmosphere; Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lithium aluminium tetrahydride; palladium 10% on activated carbon; ammonia; hydrogen; palladium diacetate; lithium; sodium hydride; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; chloroform-d1; ethanol; dichloromethane; water; water-d2; ethyl acetate; N,N-dimethyl-formamide; mineral oil; 5.1: |Heck Reaction;

DOI:10.1021/jo4000306

upstream raw materials:

2-bromo-4,5-dimethoxy-N-((1R,5S)-2-methylene-5-(prop-1-en-2-yl)cyclohexyl)benzene sulfonamide

N-allyl-2-bromo-4,5-dimethoxy-N-((1R,5S)-2-methylene-5-(prop-1-en-2-yl)cyclohexyl)benzene sulfonamide

(6S,7aR)-1-(2-bromo-4,5-dimethoxyphenylsulfonyl)-6-(prop-1-en-2-yl)-2,4,5,6,7,7a-hexahydro-1H-indole

(2S,4aR,10aR)-6,7-dimethoxy-4a,10-etheno-2,3,4,4a,10,10ahexahydro-1H-2-isopropenyl-9-thia-10-aza-phenanthrene 9,9-dioxide

Downstream raw materials:

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

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