methyl 1-{[5-{[(tert-butoxycarbonyl)amino]methyl}-2-methyl-4-(4-methylphenyl)-6-(2-methylpropyl)pyridin-3-yl]-acetyl}pyrrolidine-3-carboxylate

Base Information

• Chemical Name: methyl 1-{[5-{[(tert-butoxycarbonyl)amino]methyl}-2-methyl-4-(4-methylphenyl)-6-(2-methylpropyl)pyridin-3-yl]-acetyl}pyrrolidine-3-carboxylate
• CAS No.: 1262861-37-9
• Molecular Formula: C₃₁H₄₃N₃O₅
• Molecular Weight: 537.7

Synonyms:methyl 1-{[5-{[(tert-butoxycarbonyl)amino]methyl}-2-methyl-4-(4-methylphenyl)-6-(2-methylpropyl)pyridin-3-yl]-acetyl}pyrrolidine-3-carboxylate

Chemical Property of methyl 1-{[5-{[(tert-butoxycarbonyl)amino]methyl}-2-methyl-4-(4-methylphenyl)-6-(2-methylpropyl)pyridin-3-yl]-acetyl}pyrrolidine-3-carboxylate

Chemical Property:

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Technology Process of methyl 1-{[5-{[(tert-butoxycarbonyl)amino]methyl}-2-methyl-4-(4-methylphenyl)-6-(2-methylpropyl)pyridin-3-yl]-acetyl}pyrrolidine-3-carboxylate

There total 12 articles about methyl 1-{[5-{[(tert-butoxycarbonyl)amino]methyl}-2-methyl-4-(4-methylphenyl)-6-(2-methylpropyl)pyridin-3-yl]-acetyl}pyrrolidine-3-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: 34.0%

methyl pyrrolidine-3-carboxylate (98548-90-4,72057-18-2) + [5-{[(tert-butoxycarbonyl)amino]methyl}-2-methyl-4-(4-methylphenyl)-6-(2-methylpropyl)pyridin-3-yl]acetic acid (851577-69-0) → methyl 1-{[5-{[(tert-butoxycarbonyl)amino]methyl}-2-methyl-4-(4-methylphenyl)-6-(2-methylpropyl)pyridin-3-yl]-acetyl}pyrrolidine-3-carboxylate (1262861-37-9)

Guidance literature:

With HATU; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.bmc.2010.11.038

Reference yield:

5-methyl-2-[(4-methylphenyl)methylidene]-3-oxohexanenitrile (907611-08-9) → methyl 1-{[5-{[(tert-butoxycarbonyl)amino]methyl}-2-methyl-4-(4-methylphenyl)-6-(2-methylpropyl)pyridin-3-yl]-acetyl}pyrrolidine-3-carboxylate (1262861-37-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: methanol / 4 h / 80 °C

2.1: nitric acid / 1,4-dioxane / 0.75 h / 75 - 80 °C

3.1: ammonia; hydrogen / methanol; water / 5 h / 40 °C / 3750.38 Torr / Sealed tube

4.1: diisobutylaluminium hydride / toluene / -78 - 0 °C

4.2: 0 - 20 °C

5.1: sodium hydroxide / water; ethyl acetate; acetone; toluene / 0.5 h / 20 °C

6.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran; acetonitrile / 1 h / 20 °C

8.1: hydrogenchloride; water / 20 h / 90 °C

9.1: sodium hydroxide / water / pH 8

9.2: 1 h / 20 °C

10.1: HATU / N,N-dimethyl-formamide / 20 °C

With hydrogenchloride; tetrabutyl ammonium fluoride; ammonia; water; hydrogen; nitric acid; diisobutylaluminium hydride; triethylamine; HATU; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1016/j.bmc.2010.11.038

Reference yield:

methyl 5-cyano-2-methyl-4-(4-methylphenyl)-6-(2-methylpropyl)-1,4-dihydropyridine-3-carboxylate (851577-39-4) → methyl 1-{[5-{[(tert-butoxycarbonyl)amino]methyl}-2-methyl-4-(4-methylphenyl)-6-(2-methylpropyl)pyridin-3-yl]-acetyl}pyrrolidine-3-carboxylate (1262861-37-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: nitric acid / 1,4-dioxane / 0.75 h / 75 - 80 °C

2.1: ammonia; hydrogen / methanol; water / 5 h / 40 °C / 3750.38 Torr / Sealed tube

3.1: diisobutylaluminium hydride / toluene / -78 - 0 °C

3.2: 0 - 20 °C

4.1: sodium hydroxide / water; ethyl acetate; acetone; toluene / 0.5 h / 20 °C

5.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran; acetonitrile / 1 h / 20 °C

7.1: hydrogenchloride; water / 20 h / 90 °C

8.1: sodium hydroxide / water / pH 8

8.2: 1 h / 20 °C

9.1: HATU / N,N-dimethyl-formamide / 20 °C

With hydrogenchloride; tetrabutyl ammonium fluoride; ammonia; water; hydrogen; nitric acid; diisobutylaluminium hydride; triethylamine; HATU; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1016/j.bmc.2010.11.038

upstream raw materials:

methyl pyrrolidine-3-carboxylate

[5-{[(tert-butoxycarbonyl)amino]methyl}-2-methyl-4-(4-methylphenyl)-6-(2-methylpropyl)pyridin-3-yl]acetic acid

5-methyl-2-[(4-methylphenyl)methylidene]-3-oxohexanenitrile

methyl 5-cyano-2-methyl-4-(4-methylphenyl)-6-(2-methylpropyl)-1,4-dihydropyridine-3-carboxylate

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