(S,E)-tert-butyl-2-(4-(2-iodo-4,5-dimethoxyphenyl)-2-oxobut-3-enyl)piperidine-1-carboxylate

Base Information

Chemical Name:(S,E)-tert-butyl-2-(4-(2-iodo-4,5-dimethoxyphenyl)-2-oxobut-3-enyl)piperidine-1-carboxylate
CAS No.:1393603-60-5
Molecular Formula:C₂₂H₃₀INO₅
Molecular Weight:515.388
Hs Code.:

Synonyms:(S,E)-tert-butyl-2-(4-(2-iodo-4,5-dimethoxyphenyl)-2-oxobut-3-enyl)piperidine-1-carboxylate

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Chemical Property of (S,E)-tert-butyl-2-(4-(2-iodo-4,5-dimethoxyphenyl)-2-oxobut-3-enyl)piperidine-1-carboxylate

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Technology Process of (S,E)-tert-butyl-2-(4-(2-iodo-4,5-dimethoxyphenyl)-2-oxobut-3-enyl)piperidine-1-carboxylate

There total 7 articles about (S,E)-tert-butyl-2-(4-(2-iodo-4,5-dimethoxyphenyl)-2-oxobut-3-enyl)piperidine-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: 92.0%

: 1214914-34-7
(S)-2-(2-oxo-propyl)-piperidine-1-carboxylic acid tert-butyl ester

: 61203-53-0
2-iodo-4,5-dimethoxybenzaldehyde

: 1393603-60-5
(S,E)-tert-butyl-2-(4-(2-iodo-4,5-dimethoxyphenyl)-2-oxobut-3-enyl)piperidine-1-carboxylate

Guidance literature:: With sodium hydroxide; In methanol; at 55 ℃; for 16h;
DOI:10.1039/c2ob25880c

Reference yield:

: 1484-84-0
2(RS)-(2-hydroxyethyl)piperidine

: 1393603-60-5
(S,E)-tert-butyl-2-(4-(2-iodo-4,5-dimethoxyphenyl)-2-oxobut-3-enyl)piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: tetrahydrofuran; methanol / 0.5 h / 35 - 55 °C / Resolution of racemate

2.1: triethylamine / dichloromethane / 20 °C

3.1: phosgene; dimethyl sulfoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere

3.2: 4 h / 20 °C / Inert atmosphere

4.1: tetrahydrofuran; diethyl ether / 4.5 h / -78 - 20 °C / Inert atmosphere

5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 20 °C

6.1: sodium hydroxide / methanol / 16 h / 55 °C

With phosgene; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 3.1: Swern oxidation / 3.2: Swern oxidation;
DOI:10.1039/c2ob25880c

Reference yield:

: 1007600-14-7
N-acetyl-L-leucine (S)-2-piperidineethanol

: 1393603-60-5
(S,E)-tert-butyl-2-(4-(2-iodo-4,5-dimethoxyphenyl)-2-oxobut-3-enyl)piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: triethylamine / dichloromethane / 20 °C

2.1: phosgene; dimethyl sulfoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere

2.2: 4 h / 20 °C / Inert atmosphere

3.1: tetrahydrofuran; diethyl ether / 4.5 h / -78 - 20 °C / Inert atmosphere

4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 20 °C

5.1: sodium hydroxide / methanol / 16 h / 55 °C

With phosgene; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 2.1: Swern oxidation / 2.2: Swern oxidation;
DOI:10.1039/c2ob25880c