methyl (1R,2S)-2-{3-[(tert-butoxycarbonyl)amino]propyl}-1-(1-phenyl-1H-imidazol-4-yl)cyclopropane carboxylate

Base Information

• Chemical Name: methyl (1R,2S)-2-{3-[(tert-butoxycarbonyl)amino]propyl}-1-(1-phenyl-1H-imidazol-4-yl)cyclopropane carboxylate
• CAS No.: 1334541-16-0
• Molecular Formula: C₂₂H₂₉N₃O₄
• Molecular Weight: 399.49

Synonyms:methyl (1R,2S)-2-{3-[(tert-butoxycarbonyl)amino]propyl}-1-(1-phenyl-1H-imidazol-4-yl)cyclopropane carboxylate

Chemical Property of methyl (1R,2S)-2-{3-[(tert-butoxycarbonyl)amino]propyl}-1-(1-phenyl-1H-imidazol-4-yl)cyclopropane carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of methyl (1R,2S)-2-{3-[(tert-butoxycarbonyl)amino]propyl}-1-(1-phenyl-1H-imidazol-4-yl)cyclopropane carboxylate

There total 7 articles about methyl (1R,2S)-2-{3-[(tert-butoxycarbonyl)amino]propyl}-1-(1-phenyl-1H-imidazol-4-yl)cyclopropane 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:

di-tert-butyl dicarbonate (24424-99-5) + methyl (1R,2S)-2-(2-cyanoethyl)-1-(1-phenyl-1H-imidazol-4-yl)cyclopropane carboxylate (1334541-15-9) → methyl (1R,2S)-2-{3-[(tert-butoxycarbonyl)amino]propyl}-1-(1-phenyl-1H-imidazol-4-yl)cyclopropane carboxylate (1334541-16-0) + methyl (1S,2R)-2-{3-[(tert-butoxycarbonyl)amino]propyl}-1-(1-phenyl-1H-imidazol-4-yl)cyclopropane carboxylate

Guidance literature:

di-tert-butyl dicarbonate; methyl (1R,2S)-2-(2-cyanoethyl)-1-(1-phenyl-1H-imidazol-4-yl)cyclopropane carboxylate; With lithium borohydride; nickel(II) chloride hexahydrate; In methanol; at 0 - 20 ℃; for 16.3h;

In ethanol; hexane; Resolution of racemate;

Reference yield:

phenylboronic acid (98-80-6) → methyl (1R,2S)-2-{3-[(tert-butoxycarbonyl)amino]propyl}-1-(1-phenyl-1H-imidazol-4-yl)cyclopropane carboxylate (1334541-16-0) + methyl (1S,2R)-2-{3-[(tert-butoxycarbonyl)amino]propyl}-1-(1-phenyl-1H-imidazol-4-yl)cyclopropane carboxylate

Guidance literature:

Multi-step reaction with 6 steps

1.1: copper(II) sulfate; pyridine / dichloromethane / 20 °C / 760.05 Torr / Molecular sieve

2.1: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 0.75 h / 0 °C

2.2: 0 - 20 °C

3.1: sulfurous dibromide / methanol / 25.42 h / 0 - 20 °C

4.1: sodium hydride / mineral oil; tetrahydrofuran / 0.42 h / 20 °C

4.2: 3.5 h / 75 °C

5.1: water; lithium chloride / dimethyl sulfoxide; water / 3.3 h / 140 °C

5.2: CHIRALPAK IC / Resolution of racemate

6.1: lithium borohydride; nickel(II) chloride hexahydrate / methanol / 16.3 h / 0 - 20 °C

6.2: CHIRALPAK IC / Resolution of racemate

With pyridine; lithium borohydride; sulfurous dibromide; nickel(II) chloride hexahydrate; water; sodium hexamethyldisilazane; sodium hydride; copper(II) sulfate; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; toluene; mineral oil;

Reference yield:

4-cyanomethylimidazole (18502-05-1) → methyl (1R,2S)-2-{3-[(tert-butoxycarbonyl)amino]propyl}-1-(1-phenyl-1H-imidazol-4-yl)cyclopropane carboxylate (1334541-16-0) + methyl (1S,2R)-2-{3-[(tert-butoxycarbonyl)amino]propyl}-1-(1-phenyl-1H-imidazol-4-yl)cyclopropane carboxylate

Guidance literature:

Multi-step reaction with 6 steps

1.1: copper(II) sulfate; pyridine / dichloromethane / 20 °C / 760.05 Torr / Molecular sieve

2.1: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 0.75 h / 0 °C

2.2: 0 - 20 °C

3.1: sulfurous dibromide / methanol / 25.42 h / 0 - 20 °C

4.1: sodium hydride / mineral oil; tetrahydrofuran / 0.42 h / 20 °C

4.2: 3.5 h / 75 °C

5.1: water; lithium chloride / dimethyl sulfoxide; water / 3.3 h / 140 °C

5.2: CHIRALPAK IC / Resolution of racemate

6.1: lithium borohydride; nickel(II) chloride hexahydrate / methanol / 16.3 h / 0 - 20 °C

6.2: CHIRALPAK IC / Resolution of racemate

With pyridine; lithium borohydride; sulfurous dibromide; nickel(II) chloride hexahydrate; water; sodium hexamethyldisilazane; sodium hydride; copper(II) sulfate; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; toluene; mineral oil;

upstream raw materials:

methyl (1R,2S)-2-(3-tert-butoxy-2-cyano-3-oxopropyl)-1-(1-phenyl-1H-imidazol-4-yl)cyclopropane carboxylate

di-tert-butyl dicarbonate

methyl (1R,2S)-2-(2-cyanoethyl)-1-(1-phenyl-1H-imidazol-4-yl)cyclopropane carboxylate

4-cyanomethylimidazole

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