(3aR,6S,7aR)-benzyl 3a-(3,4-dimethoxyphenyl)-6-hydroxyoctahydro-1H-indole-1-carboxylate

Base Information

Chemical Name:(3aR,6S,7aR)-benzyl 3a-(3,4-dimethoxyphenyl)-6-hydroxyoctahydro-1H-indole-1-carboxylate
CAS No.:1427435-87-7
Molecular Formula:C₂₄H₂₉NO₅
Molecular Weight:411.498
Hs Code.:

Synonyms:(3aR,6S,7aR)-benzyl 3a-(3,4-dimethoxyphenyl)-6-hydroxyoctahydro-1H-indole-1-carboxylate

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Chemical Property of (3aR,6S,7aR)-benzyl 3a-(3,4-dimethoxyphenyl)-6-hydroxyoctahydro-1H-indole-1-carboxylate

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Technology Process of (3aR,6S,7aR)-benzyl 3a-(3,4-dimethoxyphenyl)-6-hydroxyoctahydro-1H-indole-1-carboxylate

There total 9 articles about (3aR,6S,7aR)-benzyl 3a-(3,4-dimethoxyphenyl)-6-hydroxyoctahydro-1H-indole-1-carboxylate 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: 28.0%

: 1427435-83-3
(2S,4aR,10aR)-2-acetoxy-6,7-dimethoxy-4a,10-ethano-2,3,4,4a,10,10a-hexahydro-1H-9-thia-10-aza-phenanthrene-9,9-dioxide

: 501-53-1,94274-21-2
benzyl chloroformate

: 1427435-86-6
(3aR,6S,7aR)-benzyl 6-hydroxy-3a-(4-methoxyphenyl)octahydro-1Hindole-1-carboxylate

: 1427435-87-7
(3aR,6S,7aR)-benzyl 3a-(3,4-dimethoxyphenyl)-6-hydroxyoctahydro-1H-indole-1-carboxylate

Guidance literature:: (2S,4aR,10aR)-2-acetoxy-6,7-dimethoxy-4a,10-ethano-2,3,4,4a,10,10a-hexahydro-1H-9-thia-10-aza-phenanthrene-9,9-dioxide; With ammonia; lithium; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

benzyl chloroformate; With potassium carbonate; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1021/jo4000306

Reference yield:

: 2,2,2-trichloro-N-((5S)-2-methylene-5-(prop-1-en-2-yl)cyclohexyl)acetamide

: 1427435-87-7
(3aR,6S,7aR)-benzyl 3a-(3,4-dimethoxyphenyl)-6-hydroxyoctahydro-1H-indole-1-carboxylate

Guidance literature:: Multi-step reaction with 9 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

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 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

Reference yield:

: 1427435-79-7
(6S,7aR)-1-(2-bromo-4,5-dimethoxyphenylsulfonyl)-6-(prop-1-en-2-yl)-2,4,5,6,7,7a-hexahydro-1H-indole

: 1427435-87-7
(3aR,6S,7aR)-benzyl 3a-(3,4-dimethoxyphenyl)-6-hydroxyoctahydro-1H-indole-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

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

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 15 h / 20 °C

2.2: 15 h / 0 - 20 °C

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

4.1: 3-chloro-benzenecarboperoxoic acid / chloroform-d1; water-d2 / 48 h / 20 °C

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

5.2: 4 h / 20 °C

With 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; 1.1: |Heck Reaction;
DOI:10.1021/jo4000306