tert-butyl (S)-1-[1-(3,4-dihydroquinolin-1(2H)-yl)-1-oxopropan-2-ylcarbamoyl]-2-phenylethylcarbamate

Base Information

• Chemical Name: tert-butyl (S)-1-[1-(3,4-dihydroquinolin-1(2H)-yl)-1-oxopropan-2-ylcarbamoyl]-2-phenylethylcarbamate
• CAS No.: 1273503-42-6
• Molecular Formula: C₂₆H₃₃N₃O₄
• Molecular Weight: 451.566

Synonyms:tert-butyl (S)-1-[1-(3,4-dihydroquinolin-1(2H)-yl)-1-oxopropan-2-ylcarbamoyl]-2-phenylethylcarbamate

Chemical Property of tert-butyl (S)-1-[1-(3,4-dihydroquinolin-1(2H)-yl)-1-oxopropan-2-ylcarbamoyl]-2-phenylethylcarbamate

Chemical Property:

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Technology Process of tert-butyl (S)-1-[1-(3,4-dihydroquinolin-1(2H)-yl)-1-oxopropan-2-ylcarbamoyl]-2-phenylethylcarbamate

There total 6 articles about tert-butyl (S)-1-[1-(3,4-dihydroquinolin-1(2H)-yl)-1-oxopropan-2-ylcarbamoyl]-2-phenylethylcarbamate 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: 78.0%

tert-butyl (S)-1-[2-(3,4-dihydroquinolin-1(2H)-yl)-2-oxoethylcarbamoyl]-2-phenylethylcarbamate (1273503-18-6) + methyl iodide (74-88-4) → tert-butyl (S)-1-[1-(3,4-dihydroquinolin-1(2H)-yl)-1-oxopropan-2-ylcarbamoyl]-2-phenylethylcarbamate (1273503-42-6)

Guidance literature:

tert-butyl (S)-1-[2-(3,4-dihydroquinolin-1(2H)-yl)-2-oxoethylcarbamoyl]-2-phenylethylcarbamate; With zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at 20 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.1039/c0ob00628a

Reference yield:

1,2,3,4-tetrahydroisoquinoline (635-46-1) → tert-butyl (S)-1-[1-(3,4-dihydroquinolin-1(2H)-yl)-1-oxopropan-2-ylcarbamoyl]-2-phenylethylcarbamate (1273503-42-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 4-methyl-morpholine; chloroformic acid ethyl ester / tetrahydrofuran / 0.17 h / -20 °C / Inert atmosphere

1.2: 0.25 h / -20 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / methanol / Inert atmosphere

3.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

3.2: 0.17 h / 0 °C / Inert atmosphere

4.1: palladium 10% on activated carbon; hydrogen / methanol / Inert atmosphere

5.1: triethylamine / tetrahydrofuran / 0 °C / Inert atmosphere

5.2: 6 h / Inert atmosphere

6.1: zinc(II) chloride; lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

6.2: 20 °C / Inert atmosphere

With 4-methyl-morpholine; palladium 10% on activated carbon; hydrogen; chloroformic acid ethyl ester; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; N-ethyl-N,N-diisopropylamine; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1039/c0ob00628a

Reference yield:

benzyl [2-(3,4-dihydroquinolin-1(2H)-yl)-2-oxoethyl]carbamate → tert-butyl (S)-1-[1-(3,4-dihydroquinolin-1(2H)-yl)-1-oxopropan-2-ylcarbamoyl]-2-phenylethylcarbamate (1273503-42-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: palladium 10% on activated carbon; hydrogen / methanol / Inert atmosphere

2.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

2.2: 0.17 h / 0 °C / Inert atmosphere

3.1: palladium 10% on activated carbon; hydrogen / methanol / Inert atmosphere

4.1: triethylamine / tetrahydrofuran / 0 °C / Inert atmosphere

4.2: 6 h / Inert atmosphere

5.1: zinc(II) chloride; lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

5.2: 20 °C / Inert atmosphere

With palladium 10% on activated carbon; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; N-ethyl-N,N-diisopropylamine; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1039/c0ob00628a

upstream raw materials:

1,2,3,4-tetrahydroisoquinoline

benzyl (S)-1-(2-(3,4-dihydroquinolin-1(2H)-yl)-2-oxoethylcarbamoyl)-2 phenylethylcarbamate

tert-butyl (S)-1-[2-(3,4-dihydroquinolin-1(2H)-yl)-2-oxoethylcarbamoyl]-2-phenylethylcarbamate

methyl iodide

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