(2S,2'S)-N,N'-(ethane-1,2-diyl)bis(1-benzylpyrrolidine-2-carboxamide)

Base Information

• Chemical Name: (2S,2'S)-N,N'-(ethane-1,2-diyl)bis(1-benzylpyrrolidine-2-carboxamide)
• CAS No.: 289480-96-2
• Molecular Formula: C₂₆H₃₄N₄O₂
• Molecular Weight: 434.582
• Mol file: 289480-96-2.mol

Synonyms:(2S,2'S)-N,N'-(ethane-1,2-diyl)bis(1-benzylpyrrolidine-2-carboxamide)

Chemical Property of (2S,2'S)-N,N'-(ethane-1,2-diyl)bis(1-benzylpyrrolidine-2-carboxamide)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,2'S)-N,N'-(ethane-1,2-diyl)bis(1-benzylpyrrolidine-2-carboxamide)

There total 7 articles about (2S,2'S)-N,N'-(ethane-1,2-diyl)bis(1-benzylpyrrolidine-2-carboxamide) 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: 97.0%

benzyl bromide (100-39-0) + N,N'-bis[(S)-prolyl]-1,2-ethylenediamine (54985-58-9) → (2S,2'S)-N,N'-(ethane-1,2-diyl)bis(1-benzylpyrrolidine-2-carboxamide) (289480-96-2)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1016/S0022-328X(00)00083-8

Reference yield:

N,N'-bis[(S)-N-benzyloxycarbonylprolyl]-1,2-ethylenediamine (102981-31-7,54985-57-8) → (2S,2'S)-N,N'-(ethane-1,2-diyl)bis(1-benzylpyrrolidine-2-carboxamide) (289480-96-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / cyclohexene / Pd-C / 1 h / Heating

2: 97 percent / Et₃N / tetrahydrofuran / 2 h / 0 °C

With triethylamine; cyclohexene; palladium on activated charcoal; In tetrahydrofuran; 1: Reduction / 2: Alkylation;

DOI:10.1016/S0022-328X(00)00083-8

Reference yield:

(S)-2-Ethoxycarbonyloxycarbonyl-pyrrolidine-1-carboxylic acid benzyl ester → (2S,2'S)-N,N'-(ethane-1,2-diyl)bis(1-benzylpyrrolidine-2-carboxamide) (289480-96-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 3.6 g / tetrahydrofuran / 1 h / 0 °C

2: 94 percent / cyclohexene / Pd-C / 1 h / Heating

3: 97 percent / Et₃N / tetrahydrofuran / 2 h / 0 °C

With triethylamine; cyclohexene; palladium on activated charcoal; In tetrahydrofuran; 1: Acylation / 2: Reduction / 3: Alkylation;

DOI:10.1016/S0022-328X(00)00083-8

upstream raw materials:

benzyl bromide

N,N'-bis[(S)-prolyl]-1,2-ethylenediamine

N,N'-bis[(S)-N-benzyloxycarbonylprolyl]-1,2-ethylenediamine

N-Benzyloxycarbonyl-L-proline

Downstream raw materials:

N,N'-bis{[(S)-N-benzyl-pyrrolidin-2-yl]methyl}ethylenediamine