methyl (7R)-14-cyclohexyl-7-{[2-(1,3-dioxo-1,3dihydro-2H-isoindol-2-yl)ethyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Base Information

Chemical Name:methyl (7R)-14-cyclohexyl-7-{[2-(1,3-dioxo-1,3dihydro-2H-isoindol-2-yl)ethyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate
CAS No.:1267498-45-2
Molecular Formula:C₃₅H₃₅N₃O₅
Molecular Weight:577.68
Hs Code.:

Synonyms:methyl (7R)-14-cyclohexyl-7-{[2-(1,3-dioxo-1,3dihydro-2H-isoindol-2-yl)ethyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

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Chemical Property of methyl (7R)-14-cyclohexyl-7-{[2-(1,3-dioxo-1,3dihydro-2H-isoindol-2-yl)ethyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

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Technology Process of methyl (7R)-14-cyclohexyl-7-{[2-(1,3-dioxo-1,3dihydro-2H-isoindol-2-yl)ethyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

There total 6 articles about methyl (7R)-14-cyclohexyl-7-{[2-(1,3-dioxo-1,3dihydro-2H-isoindol-2-yl)ethyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-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: 85.0%

: 2-(2,2-dihydroxyethyl)isoindole-1,3-dione

: 1267509-98-7
methyl (7R)-7-amino-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate hydrochloride

: 1267498-45-2
methyl (7R)-14-cyclohexyl-7-{[2-(1,3-dioxo-1,3dihydro-2H-isoindol-2-yl)ethyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Guidance literature:: 2-(2,2-dihydroxyethyl)isoindole-1,3-dione; methyl (7R)-7-amino-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate hydrochloride; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 15 ℃; for 0.5h; Large scale reaction;

With sodium tris(acetoxy)borohydride; In dichloromethane; at 15 ℃; for 2.08333h; optical yield given as %ee; Further stages; Large scale reaction;
DOI:10.1021/op200002u

Reference yield:

: 886041-53-8
3-cyclohexyl-2-{2-[(2S)-oxiran-2-ylmethoxy]phenyl}-1H-indole-6-carboxylic acid methyl ester

: 1267498-45-2
methyl (7R)-14-cyclohexyl-7-{[2-(1,3-dioxo-1,3dihydro-2H-isoindol-2-yl)ethyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: caesium carbonate / N,N-dimethyl acetamide / 2.5 h / 65 °C / Large scale reaction

2.1: di-isopropyl azodicarboxylate; N-ethyl-N,N-diisopropylamine; triphenylphosphine / tetrahydrofuran / 0.42 h / 10 - 15 °C / Large scale reaction

2.2: 2.67 h / 15 - 25 °C / Large scale reaction

3.1: triphenylphosphine / tetrahydrofuran / 8.5 h / 25 °C / Large scale reaction

3.2: 18 h / 50 °C / Large scale reaction

4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 15 °C / Large scale reaction

4.2: 2.08 h / 15 °C / Large scale reaction

With di-isopropyl azodicarboxylate; caesium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; 2.1: Mitsunobu reaction / 2.2: Mitsunobu reaction / 3.1: Staudinger reaction / 3.2: Staudinger reaction;
DOI:10.1021/op200002u

Reference yield:

: 886041-54-9
methyl (7S)-14-cyclohexyl-7-hydroxy-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

: 1267498-45-2
methyl (7R)-14-cyclohexyl-7-{[2-(1,3-dioxo-1,3dihydro-2H-isoindol-2-yl)ethyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: di-isopropyl azodicarboxylate; N-ethyl-N,N-diisopropylamine; triphenylphosphine / tetrahydrofuran / 0.42 h / 10 - 15 °C / Large scale reaction

1.2: 2.67 h / 15 - 25 °C / Large scale reaction

2.1: triphenylphosphine / tetrahydrofuran / 8.5 h / 25 °C / Large scale reaction

2.2: 18 h / 50 °C / Large scale reaction

3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 15 °C / Large scale reaction

3.2: 2.08 h / 15 °C / Large scale reaction

With di-isopropyl azodicarboxylate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; 1.1: Mitsunobu reaction / 1.2: Mitsunobu reaction / 2.1: Staudinger reaction / 2.2: Staudinger reaction;
DOI:10.1021/op200002u