(1E)-N-tert-butoxycarbonyl-2-(6′-phenylhexa-1′,3′-dien-1′-yloxy)piperidine

Base Information

Chemical Name:(1E)-N-tert-butoxycarbonyl-2-(6′-phenylhexa-1′,3′-dien-1′-yloxy)piperidine
CAS No.:1427072-58-9
Molecular Formula:C₂₂H₃₁NO₃
Molecular Weight:357.493
Hs Code.:

Synonyms:(1E)-N-tert-butoxycarbonyl-2-(6′-phenylhexa-1′,3′-dien-1′-yloxy)piperidine

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Chemical Property of (1E)-N-tert-butoxycarbonyl-2-(6′-phenylhexa-1′,3′-dien-1′-yloxy)piperidine

Chemical Property:

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Technology Process of (1E)-N-tert-butoxycarbonyl-2-(6′-phenylhexa-1′,3′-dien-1′-yloxy)piperidine

There total 8 articles about (1E)-N-tert-butoxycarbonyl-2-(6′-phenylhexa-1′,3′-dien-1′-yloxy)piperidine 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:

: 1427072-47-6
(Z)-N-tert-butoxycarbonyl-2-(4’-methoxy-6’-phenylhex-2’-en-1’-yloxy)piperidine

: 1427072-58-9
(1E)-N-tert-butoxycarbonyl-2-(6′-phenylhexa-1′,3′-dien-1′-yloxy)piperidine

: 1427072-59-0
(1E)-N-tert-butoxycarbonyl-2-(6′-phenylhexa-1′,3′-dien-1′-yloxy)piperidine

: 1427072-60-3
(1Z)-N-tert-butoxycarbonyl-2-(6′-phenylhexa-1′,3′-dien-1′-yloxy)piperidine

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 12h; Overall yield = 81 %; stereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2013.01.088

Reference yield:

: 675-20-7
piperidin-2-one

: 1427072-58-9
(1E)-N-tert-butoxycarbonyl-2-(6′-phenylhexa-1′,3′-dien-1′-yloxy)piperidine

: 1427072-59-0
(1E)-N-tert-butoxycarbonyl-2-(6′-phenylhexa-1′,3′-dien-1′-yloxy)piperidine

: 1427072-60-3
(1Z)-N-tert-butoxycarbonyl-2-(6′-phenylhexa-1′,3′-dien-1′-yloxy)piperidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / Inert atmosphere

1.2: 2 h / 0 °C / Inert atmosphere

2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / dichloromethane; toluene / 2 h / -78 °C

3.1: boron trifluoride diethyl etherate / dichloromethane / 20 °C / Molecular sieve

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; boron trifluoride diethyl etherate; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1016/j.tet.2013.01.088

Reference yield:

: 85908-96-9
2-oxopiperidine-1-carboxylic acid tert-butyl ester

: 1427072-58-9
(1E)-N-tert-butoxycarbonyl-2-(6′-phenylhexa-1′,3′-dien-1′-yloxy)piperidine

: 1427072-59-0
(1E)-N-tert-butoxycarbonyl-2-(6′-phenylhexa-1′,3′-dien-1′-yloxy)piperidine

: 1427072-60-3
(1Z)-N-tert-butoxycarbonyl-2-(6′-phenylhexa-1′,3′-dien-1′-yloxy)piperidine

Guidance literature:: Multi-step reaction with 3 steps

1: sodium bis(2-methoxyethoxy)aluminium dihydride / dichloromethane; toluene / 2 h / -78 °C

2: boron trifluoride diethyl etherate / dichloromethane / 20 °C / Molecular sieve

3: 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; boron trifluoride diethyl etherate; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1016/j.tet.2013.01.088