cis-(4S,5S)-1,5-dibenzyl-3-phenyl-4-((2,2,6,6-tetramethylpiperidin-1-yloxy)methyl)imidazolidin-2-one

Base Information

• Chemical Name: cis-(4S,5S)-1,5-dibenzyl-3-phenyl-4-((2,2,6,6-tetramethylpiperidin-1-yloxy)methyl)imidazolidin-2-one
• CAS No.: 1324004-32-1
• Molecular Formula: C₃₃H₄₁N₃O₂
• Molecular Weight: 511.707

Synonyms:cis-(4S,5S)-1,5-dibenzyl-3-phenyl-4-((2,2,6,6-tetramethylpiperidin-1-yloxy)methyl)imidazolidin-2-one

Chemical Property of cis-(4S,5S)-1,5-dibenzyl-3-phenyl-4-((2,2,6,6-tetramethylpiperidin-1-yloxy)methyl)imidazolidin-2-one

Chemical Property:

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Technology Process of cis-(4S,5S)-1,5-dibenzyl-3-phenyl-4-((2,2,6,6-tetramethylpiperidin-1-yloxy)methyl)imidazolidin-2-one

There total 5 articles about cis-(4S,5S)-1,5-dibenzyl-3-phenyl-4-((2,2,6,6-tetramethylpiperidin-1-yloxy)methyl)imidazolidin-2-one 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:

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2,45842-10-2,126517-51-9,25657-03-8,26933-82-4,54637-06-8,64104-42-3) + (S)-1-benzyl-3-phenyl-1-(1-phenylbut-3-en-2-yl)urea (1324003-93-1) → cis-(4S,5S)-1,5-dibenzyl-3-phenyl-4-((2,2,6,6-tetramethylpiperidin-1-yloxy)methyl)imidazolidin-2-one (1324004-32-1) + trans-(4R,5S)-1,5-dibenzyl-3-phenyl-4-((2,2,6,6-tetramethylpiperidin-1-yloxy)methyl)imidazolidin-2-one (1324004-29-6)

Guidance literature:

With 2-(2-(4,5-dihydrooxazol-2-yl)propan-2-yl)-4,5-dihydrooxazole; oxygen; copper(II) bis(trifluoromethanesulfonate); potassium carbonate; In α,α,α-trifluorotoluene; at 120 ℃; for 24h; under 760.051 Torr; optical yield given as %de; diastereoselective reaction;

DOI:10.1002/ejoc.201100444

Reference yield:

C17H17N → cis-(4S,5S)-1,5-dibenzyl-3-phenyl-4-((2,2,6,6-tetramethylpiperidin-1-yloxy)methyl)imidazolidin-2-one (1324004-32-1) + trans-(4R,5S)-1,5-dibenzyl-3-phenyl-4-((2,2,6,6-tetramethylpiperidin-1-yloxy)methyl)imidazolidin-2-one (1324004-29-6)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tetrahydroborate / methanol / 20 °C

2: dichloromethane / 2 h / 20 °C

3: 2-(2-(4,5-dihydrooxazol-2-yl)propan-2-yl)-4,5-dihydrooxazole; oxygen; copper(II) bis(trifluoromethanesulfonate); potassium carbonate / α,α,α-trifluorotoluene / 24 h / 120 °C / 760.05 Torr

With sodium tetrahydroborate; 2-(2-(4,5-dihydrooxazol-2-yl)propan-2-yl)-4,5-dihydrooxazole; oxygen; copper(II) bis(trifluoromethanesulfonate); potassium carbonate; In methanol; dichloromethane; α,α,α-trifluorotoluene;

DOI:10.1002/ejoc.201100444

Reference yield:

(S)-1-phenylbut-3-en-2-amine (126410-30-8) → cis-(4S,5S)-1,5-dibenzyl-3-phenyl-4-((2,2,6,6-tetramethylpiperidin-1-yloxy)methyl)imidazolidin-2-one (1324004-32-1) + trans-(4R,5S)-1,5-dibenzyl-3-phenyl-4-((2,2,6,6-tetramethylpiperidin-1-yloxy)methyl)imidazolidin-2-one (1324004-29-6)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / methanol / 0.33 h / 20 °C

2: sodium tetrahydroborate / methanol / 20 °C

3: dichloromethane / 2 h / 20 °C

4: 2-(2-(4,5-dihydrooxazol-2-yl)propan-2-yl)-4,5-dihydrooxazole; oxygen; copper(II) bis(trifluoromethanesulfonate); potassium carbonate / α,α,α-trifluorotoluene / 24 h / 120 °C / 760.05 Torr

With sodium tetrahydroborate; 2-(2-(4,5-dihydrooxazol-2-yl)propan-2-yl)-4,5-dihydrooxazole; oxygen; copper(II) bis(trifluoromethanesulfonate); potassium carbonate; triethylamine; In methanol; dichloromethane; α,α,α-trifluorotoluene;

DOI:10.1002/ejoc.201100444

upstream raw materials:

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

(S)-1-benzyl-3-phenyl-1-(1-phenylbut-3-en-2-yl)urea

(S)-1-phenylbut-3-en-2-amine

benzaldehyde

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