(E)-1-(tert-butoxycarbonyl)-3-[4-hydroxy-4-(4-nitrophenyl)butan-2-ylidene]indolin-2-one

Base Information

Chemical Name:(E)-1-(tert-butoxycarbonyl)-3-[4-hydroxy-4-(4-nitrophenyl)butan-2-ylidene]indolin-2-one
CAS No.:1374606-11-7
Molecular Formula:C₂₃H₂₄N₂O₆
Molecular Weight:424.453
Hs Code.:

Synonyms:(E)-1-(tert-butoxycarbonyl)-3-[4-hydroxy-4-(4-nitrophenyl)butan-2-ylidene]indolin-2-one

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (E)-1-(tert-butoxycarbonyl)-3-[4-hydroxy-4-(4-nitrophenyl)butan-2-ylidene]indolin-2-one

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Technology Process of (E)-1-(tert-butoxycarbonyl)-3-[4-hydroxy-4-(4-nitrophenyl)butan-2-ylidene]indolin-2-one

There total 8 articles about (E)-1-(tert-butoxycarbonyl)-3-[4-hydroxy-4-(4-nitrophenyl)butan-2-ylidene]indolin-2-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: 59.0%

: 1374605-95-4
1-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]-3-(prop-1-en-2-yl)-1H-indole

: 555-16-8
4-nitrobenzaldehdye

: 1374606-11-7
(E)-1-(tert-butoxycarbonyl)-3-[4-hydroxy-4-(4-nitrophenyl)butan-2-ylidene]indolin-2-one

: 1374606-02-6
(+/-)-(Z)-1-(tert-butoxycarbonyl)-3-[4-hydroxy-4-(4-nitrophenyl)butan-2-ylidene]indolin-2-one

Guidance literature:: With tetrachlorosilane; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at -20 ℃; for 12h; optical yield given as %de; Inert atmosphere;
DOI:10.1002/ejoc.201101446

Reference yield:

: 1374605-95-4
1-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]-3-(prop-1-en-2-yl)-1H-indole

: 555-16-8
4-nitrobenzaldehdye

: 1374606-20-8
(4'R)-(Z)-1-(tert-butoxycarbonyl)-3-[4-hydroxy-4-(4-nitrophenyl)butan-2-ylidene]indolin-2-one

: 1374606-11-7
(E)-1-(tert-butoxycarbonyl)-3-[4-hydroxy-4-(4-nitrophenyl)butan-2-ylidene]indolin-2-one

Guidance literature:: With tetrachlorosilane; C₄₉H₅₅N₇O₂P₂; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at -78 ℃; optical yield given as %ee; stereoselective reaction; Inert atmosphere;
DOI:10.1002/ejoc.201101446

Reference yield:

: 59-48-3
2-oxoindole

: 1374606-11-7
(E)-1-(tert-butoxycarbonyl)-3-[4-hydroxy-4-(4-nitrophenyl)butan-2-ylidene]indolin-2-one

: 1374606-02-6
(+/-)-(Z)-1-(tert-butoxycarbonyl)-3-[4-hydroxy-4-(4-nitrophenyl)butan-2-ylidene]indolin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: piperidine / ethanol / 4 h / 23 °C / Inert atmosphere

2: dmap / acetonitrile / 2 h / 20 °C / Inert atmosphere

3: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

4: tetrachlorosilane; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 12 h / -20 °C / Inert atmosphere

With piperidine; dmap; tetrachlorosilane; triethylamine; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 4: Mukaiyama aldol reaction;
DOI:10.1002/ejoc.201101446