(6S,10S)-methyl 12-benzyl-9-hydroxy-2-methoxy-6,7,10,11-tetrahydro-5H-6,10-epimino-cycloocta[b]indole-8-carboxylate

Base Information

Chemical Name:(6S,10S)-methyl 12-benzyl-9-hydroxy-2-methoxy-6,7,10,11-tetrahydro-5H-6,10-epimino-cycloocta[b]indole-8-carboxylate
CAS No.:600136-03-6
Molecular Formula:C₂₄H₂₄N₂O₄
Molecular Weight:404.466
Hs Code.:

Synonyms:(6S,10S)-methyl 12-benzyl-9-hydroxy-2-methoxy-6,7,10,11-tetrahydro-5H-6,10-epimino-cycloocta[b]indole-8-carboxylate

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Chemical Property of (6S,10S)-methyl 12-benzyl-9-hydroxy-2-methoxy-6,7,10,11-tetrahydro-5H-6,10-epimino-cycloocta[b]indole-8-carboxylate

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Technology Process of (6S,10S)-methyl 12-benzyl-9-hydroxy-2-methoxy-6,7,10,11-tetrahydro-5H-6,10-epimino-cycloocta[b]indole-8-carboxylate

There total 22 articles about (6S,10S)-methyl 12-benzyl-9-hydroxy-2-methoxy-6,7,10,11-tetrahydro-5H-6,10-epimino-cycloocta[b]indole-8-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:

: 21987-25-7
5-methoxy-3-methyl-1H-indole

: 600136-03-6
(6S,10S)-methyl 12-benzyl-9-hydroxy-2-methoxy-6,7,10,11-tetrahydro-5H-6,10-epimino-cycloocta[b]indole-8-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 95 percent / DMAP / acetonitrile / 12 h / 20 °C

2.1: N-bromosuccinimide; AIBN / CCl₄ / 0.67 h / Heating

3.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

3.2: 93 percent / tetrahydrofuran / -78 - 20 °C

4.1: 96 percent / aq. HCl / tetrahydrofuran / 0 - 20 °C

5.1: ethanol / 4.5 h / 20 °C

6.1: 2.9 g / sodium borohydride / ethanol / 1 h / -10 °C

7.1: TFA / CHCl₃ / Heating

7.2: 60 percent / xylene / 48 h / Heating

8.1: 75 percent / sodium hydride; methanol / toluene / 72 h / Heating

With hydrogenchloride; methanol; dmap; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; 2,2'-azobis(isobutyronitrile); sodium hydride; trifluoroacetic acid; In tetrahydrofuran; tetrachloromethane; ethanol; chloroform; toluene; acetonitrile; 7.1: Pictet-Spengler cyclization / 8.1: Dieckmann condensation;
DOI:10.1021/jo030055u

Reference yield:

: 16381-42-3
ethyl 5-methoxy-3-methyl-1H-indole-2-carboxylate

: 600136-03-6
(6S,10S)-methyl 12-benzyl-9-hydroxy-2-methoxy-6,7,10,11-tetrahydro-5H-6,10-epimino-cycloocta[b]indole-8-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

1.1: 100 percent / KOH / ethanol / 1 h / Heating

2.1: 93.6 percent / Cu; quinoline / 2.5 h / Heating

3.1: 95 percent / DMAP / acetonitrile / 12 h / 20 °C

4.1: N-bromosuccinimide; AIBN / CCl₄ / 0.67 h / Heating

5.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

5.2: 93 percent / tetrahydrofuran / -78 - 20 °C

6.1: 96 percent / aq. HCl / tetrahydrofuran / 0 - 20 °C

7.1: ethanol / 4.5 h / 20 °C

8.1: 2.9 g / sodium borohydride / ethanol / 1 h / -10 °C

9.1: TFA / CHCl₃ / Heating

9.2: 60 percent / xylene / 48 h / Heating

10.1: 75 percent / sodium hydride; methanol / toluene / 72 h / Heating

With quinoline; hydrogenchloride; methanol; dmap; potassium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; 2,2'-azobis(isobutyronitrile); copper; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; tetrachloromethane; ethanol; chloroform; toluene; acetonitrile; 9.1: Pictet-Spengler cyclization / 10.1: Dieckmann condensation;
DOI:10.1021/jo030055u

Reference yield:

: 168143-70-2
tert-butyl 5-methoxy-3-methyl-1H-indole-1-carboxylate

: 600136-03-6
(6S,10S)-methyl 12-benzyl-9-hydroxy-2-methoxy-6,7,10,11-tetrahydro-5H-6,10-epimino-cycloocta[b]indole-8-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: N-bromosuccinimide; AIBN / CCl₄ / 0.67 h / Heating

2.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

2.2: 93 percent / tetrahydrofuran / -78 - 20 °C

3.1: 96 percent / aq. HCl / tetrahydrofuran / 0 - 20 °C

4.1: ethanol / 4.5 h / 20 °C

5.1: 2.9 g / sodium borohydride / ethanol / 1 h / -10 °C

6.1: TFA / CHCl₃ / Heating

6.2: 60 percent / xylene / 48 h / Heating

7.1: 75 percent / sodium hydride; methanol / toluene / 72 h / Heating

With hydrogenchloride; methanol; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; 2,2'-azobis(isobutyronitrile); sodium hydride; trifluoroacetic acid; In tetrahydrofuran; tetrachloromethane; ethanol; chloroform; toluene; 6.1: Pictet-Spengler cyclization / 7.1: Dieckmann condensation;
DOI:10.1021/jo030055u