2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1-(2-chlorobenzyl)-1H-imidazole-5-carboxylic acid

Base Information

Chemical Name:2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1-(2-chlorobenzyl)-1H-imidazole-5-carboxylic acid
CAS No.:1349877-51-5
Molecular Formula:C₂₁H₂₇ClN₄O₄
Molecular Weight:434.923
Hs Code.:

Synonyms:2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1-(2-chlorobenzyl)-1H-imidazole-5-carboxylic acid

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Chemical Property of 2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1-(2-chlorobenzyl)-1H-imidazole-5-carboxylic acid

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Technology Process of 2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1-(2-chlorobenzyl)-1H-imidazole-5-carboxylic acid

There total 7 articles about 2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1-(2-chlorobenzyl)-1H-imidazole-5-carboxylic acid 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%

: 1349877-49-1
ethyl 2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1-(2-chlorobenzyl)-1H-imidazole-5-carboxylate

: 1349877-51-5
2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1-(2-chlorobenzyl)-1H-imidazole-5-carboxylic acid

Guidance literature:: ethyl 2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1-(2-chlorobenzyl)-1H-imidazole-5-carboxylate; With sodium hydroxide; In tetrahydrofuran; ethanol; at 80 ℃; for 5h;

With potassium hydrogensulfate;
DOI:10.1016/j.tet.2011.10.015

Reference yield:

: 309956-78-3,172603-05-3
(R)-piperidin-3-ylcarbamic acid tert-butyl ester

: 1349877-51-5
2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1-(2-chlorobenzyl)-1H-imidazole-5-carboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: isopropyl alcohol / 2.5 h / 20 °C

1.2: 6 h / 0 - 80 °C

2.1: potassium carbonate / acetonitrile / 72 h / 40 °C

3.1: sodium hydride / tetrahydrofuran; mineral oil / 2.5 h / 0 - 15 °C

4.1: diiodomethane; isopentyl nitrite / toluene / 9 h / 80 °C

5.1: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 20 °C

6.1: sodium hydroxide / tetrahydrofuran; ethanol / 5 h / 80 °C

With diiodomethane; palladium 10% on activated carbon; hydrogen; sodium hydride; potassium carbonate; sodium hydroxide; isopentyl nitrite; In tetrahydrofuran; methanol; ethanol; isopropyl alcohol; toluene; acetonitrile; mineral oil; 4.1: Sandmeyer reaction;
DOI:10.1016/j.tet.2011.10.015

Reference yield:

: 1349877-39-9,791076-27-2
ethyl N-[(E)-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}(cyanoimino)methyl]glycinate

: 1349877-51-5
2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1-(2-chlorobenzyl)-1H-imidazole-5-carboxylic acid

Guidance literature:: Multi-step reaction with 5 steps

1: potassium carbonate / acetonitrile / 72 h / 40 °C

2: sodium hydride / tetrahydrofuran; mineral oil / 2.5 h / 0 - 15 °C

3: diiodomethane; isopentyl nitrite / toluene / 9 h / 80 °C

4: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 20 °C

5: sodium hydroxide / tetrahydrofuran; ethanol / 5 h / 80 °C

With diiodomethane; palladium 10% on activated carbon; hydrogen; sodium hydride; potassium carbonate; sodium hydroxide; isopentyl nitrite; In tetrahydrofuran; methanol; ethanol; toluene; acetonitrile; mineral oil; 3: Sandmeyer reaction;
DOI:10.1016/j.tet.2011.10.015