tert-butyl 3-[(Z)-4-(2-methoxyethylamino)-4-phenylbut-1-enyl]-1H-indole-1-carboxylate

Base Information

Chemical Name:tert-butyl 3-[(Z)-4-(2-methoxyethylamino)-4-phenylbut-1-enyl]-1H-indole-1-carboxylate
CAS No.:1380611-56-2
Molecular Formula:C₂₆H₃₂N₂O₃
Molecular Weight:420.552
Hs Code.:

Synonyms:tert-butyl 3-[(Z)-4-(2-methoxyethylamino)-4-phenylbut-1-enyl]-1H-indole-1-carboxylate

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Chemical Property of tert-butyl 3-[(Z)-4-(2-methoxyethylamino)-4-phenylbut-1-enyl]-1H-indole-1-carboxylate

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Technology Process of tert-butyl 3-[(Z)-4-(2-methoxyethylamino)-4-phenylbut-1-enyl]-1H-indole-1-carboxylate

There total 3 articles about tert-butyl 3-[(Z)-4-(2-methoxyethylamino)-4-phenylbut-1-enyl]-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: 46.0%

: 1243146-96-4
tert-butyl 3-(1-tert-butyldimethylsilyloxyprop-2-en-1-yl)-1H-indole-1-carboxylate

: 105427-43-8
N-(2-methoxyethyl)-1-phenylmethanimine

: 1380611-56-2
tert-butyl 3-[(Z)-4-(2-methoxyethylamino)-4-phenylbut-1-enyl]-1H-indole-1-carboxylate

: 1380611-42-6
tert-butyl 3-[(E)-4-(2-methoxyethylamino)-4-phenylbut-1-enyl]-1H-indole-1-carboxylate

Guidance literature:: tert-butyl 3-(1-tert-butyldimethylsilyloxyprop-2-en-1-yl)-1H-indole-1-carboxylate; With n-butyllithium; zirconocene dichloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 3h; Inert atmosphere;

With zinc trifluoromethanesulfonate; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h; Inert atmosphere;

N-(2-methoxyethyl)-1-phenylmethanimine; In tetrahydrofuran; hexane; at 20 ℃; for 10h; optical yield given as %de; regioselective reaction; Inert atmosphere;
DOI:10.1021/ol301026w

Reference yield:

: tert-butyl 3-(1-hydroxyprop-2-en-1-yl)-1H-indole-1-carboxylate

: 1380611-56-2
tert-butyl 3-[(Z)-4-(2-methoxyethylamino)-4-phenylbut-1-enyl]-1H-indole-1-carboxylate

: 1380611-42-6
tert-butyl 3-[(E)-4-(2-methoxyethylamino)-4-phenylbut-1-enyl]-1H-indole-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / Inert atmosphere

2.1: zirconocene dichloride; n-butyllithium / tetrahydrofuran; hexane / 3 h / -78 - 20 °C / Inert atmosphere

2.2: 0.5 h / 0 °C / Inert atmosphere

2.3: 10 h / 20 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; zirconocene dichloride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;
DOI:10.1021/ol301026w

Reference yield:

: 57476-50-3
1-tert-butoxycarbonyl-3-formylindole

: 1380611-56-2
tert-butyl 3-[(Z)-4-(2-methoxyethylamino)-4-phenylbut-1-enyl]-1H-indole-1-carboxylate

: 1380611-42-6
tert-butyl 3-[(E)-4-(2-methoxyethylamino)-4-phenylbut-1-enyl]-1H-indole-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / Inert atmosphere

3.1: zirconocene dichloride; n-butyllithium / tetrahydrofuran; hexane / 3 h / -78 - 20 °C / Inert atmosphere

3.2: 0.5 h / 0 °C / Inert atmosphere

3.3: 10 h / 20 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; zirconocene dichloride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;
DOI:10.1021/ol301026w