(E)-N-tert-butoxycarbonyl-N-ethyl-1-(4'-methylpenta-1',3'-dien-1'-yloxy)-3-phenylpropan-1-amine

Base Information

Chemical Name:(E)-N-tert-butoxycarbonyl-N-ethyl-1-(4'-methylpenta-1',3'-dien-1'-yloxy)-3-phenylpropan-1-amine
CAS No.:1427072-90-9
Molecular Formula:C₂₂H₃₃NO₃
Molecular Weight:359.509
Hs Code.:

Synonyms:(E)-N-tert-butoxycarbonyl-N-ethyl-1-(4'-methylpenta-1',3'-dien-1'-yloxy)-3-phenylpropan-1-amine

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Chemical Property of (E)-N-tert-butoxycarbonyl-N-ethyl-1-(4'-methylpenta-1',3'-dien-1'-yloxy)-3-phenylpropan-1-amine

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Technology Process of (E)-N-tert-butoxycarbonyl-N-ethyl-1-(4'-methylpenta-1',3'-dien-1'-yloxy)-3-phenylpropan-1-amine

There total 6 articles about (E)-N-tert-butoxycarbonyl-N-ethyl-1-(4'-methylpenta-1',3'-dien-1'-yloxy)-3-phenylpropan-1-amine 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: 83.0%

: 1427072-85-2
(Z)-N-tert-butoxycarbonyl-N-ethyl-1-(4’-methoxy-4’-methylpent-2’-en-1’-yloxy)-3-phenylpropan-1-amine

: 1427072-90-9
(E)-N-tert-butoxycarbonyl-N-ethyl-1-(4'-methylpenta-1',3'-dien-1'-yloxy)-3-phenylpropan-1-amine

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 12h; stereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2013.01.088

Reference yield:

: 1080059-52-4
(Z)-4-methoxy-4-methylpent-2-en-1-ol

: 1427072-90-9
(E)-N-tert-butoxycarbonyl-N-ethyl-1-(4'-methylpenta-1',3'-dien-1'-yloxy)-3-phenylpropan-1-amine

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

1.2: 1 h / 0 - 20 °C / Inert atmosphere

2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere

3.1: n-butyllithium; 2,2,6,6-tetramethyl-piperidine / tetrahydrofuran; hexane / 12 h / 0 - 20 °C / Inert atmosphere

With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; sodium hydride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.tet.2013.01.088

Reference yield:

: C₁₁H₂₂O₃

: 1427072-90-9
(E)-N-tert-butoxycarbonyl-N-ethyl-1-(4'-methylpenta-1',3'-dien-1'-yloxy)-3-phenylpropan-1-amine

Guidance literature:: Multi-step reaction with 4 steps

1.1: pyridinium p-toluenesulfonate / methanol / 13 h / 20 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

2.2: 1 h / 0 - 20 °C / Inert atmosphere

3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere

4.1: n-butyllithium; 2,2,6,6-tetramethyl-piperidine / tetrahydrofuran; hexane / 12 h / 0 - 20 °C / Inert atmosphere

With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; pyridinium p-toluenesulfonate; sodium hydride; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.tet.2013.01.088