(5S,6R)-5-hydroxy-6-phenyl-3-[(S)-1-phenylethyl]-2,3,5,6-tetrahydro-1H-azocino[5,4-b]indol-4(7H)-one

Base Information

Chemical Name:(5S,6R)-5-hydroxy-6-phenyl-3-[(S)-1-phenylethyl]-2,3,5,6-tetrahydro-1H-azocino[5,4-b]indol-4(7H)-one
CAS No.:1431767-89-3
Molecular Formula:C₂₇H₂₆N₂O₂
Molecular Weight:410.516
Hs Code.:

Synonyms:(5S,6R)-5-hydroxy-6-phenyl-3-[(S)-1-phenylethyl]-2,3,5,6-tetrahydro-1H-azocino[5,4-b]indol-4(7H)-one

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Chemical Property of (5S,6R)-5-hydroxy-6-phenyl-3-[(S)-1-phenylethyl]-2,3,5,6-tetrahydro-1H-azocino[5,4-b]indol-4(7H)-one

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Technology Process of (5S,6R)-5-hydroxy-6-phenyl-3-[(S)-1-phenylethyl]-2,3,5,6-tetrahydro-1H-azocino[5,4-b]indol-4(7H)-one

There total 9 articles about (5S,6R)-5-hydroxy-6-phenyl-3-[(S)-1-phenylethyl]-2,3,5,6-tetrahydro-1H-azocino[5,4-b]indol-4(7H)-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: 80.0%

: 1431767-78-0
(5S,6R)-(tert-butyl) 5-hydroxy-4-oxo-6-phenyl-3-[(S)-1-phenylethyl]-3,4,5,6-tetrahydro-1H-azocino[5,4-b]indole-7(2H)-carboxylate

: 1431767-89-3
(5S,6R)-5-hydroxy-6-phenyl-3-[(S)-1-phenylethyl]-2,3,5,6-tetrahydro-1H-azocino[5,4-b]indol-4(7H)-one

Guidance literature:: With tetrabutyl ammonium fluoride; In dichloromethane; at 20 ℃;
DOI:10.1016/j.tetlet.2013.03.068

Reference yield:

: 3389-21-7
3-(2-bromoethyl)-1H-indole

: 1431767-89-3
(5S,6R)-5-hydroxy-6-phenyl-3-[(S)-1-phenylethyl]-2,3,5,6-tetrahydro-1H-azocino[5,4-b]indol-4(7H)-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: dmap; triethylamine / dichloromethane / 3 h / 20 °C

2.1: potassium carbonate / acetonitrile / 20 °C / Reflux

3.1: potassium carbonate / acetonitrile / 3 h / 20 °C

4.1: sodium dihydrogenphosphate dihydrate / tert-butyl alcohol; tetrahydrofuran; water / 0.25 h / 20 °C

4.2: 8 h / 0 °C

5.1: copper(II) bis(trifluoromethanesulfonate) / acetonitrile / 0.5 h

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / Reflux

With dmap; sodium dihydrogenphosphate dihydrate; tetrabutyl ammonium fluoride; copper(II) bis(trifluoromethanesulfonate); potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; water; acetonitrile; tert-butyl alcohol;
DOI:10.1055/s-0032-1316893

Reference yield:

: 131829-28-2
3-(2-bromoethyl)indole-1-carboxylic acid tert-butyl ester

: 1431767-89-3
(5S,6R)-5-hydroxy-6-phenyl-3-[(S)-1-phenylethyl]-2,3,5,6-tetrahydro-1H-azocino[5,4-b]indol-4(7H)-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium carbonate / acetonitrile / 20 °C / Reflux

2.1: potassium carbonate / acetonitrile / 3 h / 20 °C

3.1: sodium dihydrogenphosphate dihydrate / tert-butyl alcohol; tetrahydrofuran; water / 0.25 h / 20 °C

3.2: 8 h / 0 °C

4.1: copper(II) bis(trifluoromethanesulfonate) / acetonitrile / 0.5 h

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / Reflux

With sodium dihydrogenphosphate dihydrate; tetrabutyl ammonium fluoride; copper(II) bis(trifluoromethanesulfonate); potassium carbonate; In tetrahydrofuran; water; acetonitrile; tert-butyl alcohol;
DOI:10.1055/s-0032-1316893