benzyl (2S,5R)-2-{[(3S)-3,4-dimethylpiperazin-1-yl]carbonyl}-5-methylpyrrolidine-1-carboxylate

Base Information

• Chemical Name: benzyl (2S,5R)-2-{[(3S)-3,4-dimethylpiperazin-1-yl]carbonyl}-5-methylpyrrolidine-1-carboxylate
• CAS No.: 1033714-79-2
• Molecular Formula: C₂₀H₂₉N₃O₃
• Molecular Weight: 359.469

Synonyms:benzyl (2S,5R)-2-{[(3S)-3,4-dimethylpiperazin-1-yl]carbonyl}-5-methylpyrrolidine-1-carboxylate

Chemical Property of benzyl (2S,5R)-2-{[(3S)-3,4-dimethylpiperazin-1-yl]carbonyl}-5-methylpyrrolidine-1-carboxylate

Chemical Property:

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Technology Process of benzyl (2S,5R)-2-{[(3S)-3,4-dimethylpiperazin-1-yl]carbonyl}-5-methylpyrrolidine-1-carboxylate

There total 6 articles about benzyl (2S,5R)-2-{[(3S)-3,4-dimethylpiperazin-1-yl]carbonyl}-5-methylpyrrolidine-1-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: 51.0%

(2S)-1,2-dimethylpiperazine dihydrochloride (1152110-23-0,485841-50-7) + (5R)-1-[(benzyloxy)carbonyl]-5-methyl-L-proline (1033714-59-8) → benzyl (2S,5R)-2-{[(3S)-3,4-dimethylpiperazin-1-yl]carbonyl}-5-methylpyrrolidine-1-carboxylate (1033714-79-2)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1016/j.bmc.2013.04.056

Reference yield:

Cbz-L-pGlu-OH (32159-21-0) → benzyl (2S,5R)-2-{[(3S)-3,4-dimethylpiperazin-1-yl]carbonyl}-5-methylpyrrolidine-1-carboxylate (1033714-79-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: perchloric acid / water / 16 h / 20 °C

2.1: lithium triethylborohydride / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

3.1: toluene-4-sulfonic acid / 48 h / 20 °C

4.1: copper(I) bromide dimethylsulfide complex / diethyl ether / 0.5 h / -78 °C / Inert atmosphere

4.2: 16 h / -78 - 20 °C / Inert atmosphere

5.1: trifluoroacetic acid / chloroform / 16 h / 50 °C

6.1: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 20 °C

With perchloric acid; copper(I) bromide dimethylsulfide complex; lithium triethylborohydride; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; water;

DOI:10.1016/j.bmc.2013.04.056

Reference yield:

tert-butyl N-benzyloxycarbonyl-L-pyroglutamate (81470-51-1) → benzyl (2S,5R)-2-{[(3S)-3,4-dimethylpiperazin-1-yl]carbonyl}-5-methylpyrrolidine-1-carboxylate (1033714-79-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium triethylborohydride / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / 48 h / 20 °C

3.1: copper(I) bromide dimethylsulfide complex / diethyl ether / 0.5 h / -78 °C / Inert atmosphere

3.2: 16 h / -78 - 20 °C / Inert atmosphere

4.1: trifluoroacetic acid / chloroform / 16 h / 50 °C

5.1: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 20 °C

With copper(I) bromide dimethylsulfide complex; lithium triethylborohydride; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform;

DOI:10.1016/j.bmc.2013.04.056

upstream raw materials:

Cbz-L-pGlu-OH

tert-butyl N-benzyloxycarbonyl-L-pyroglutamate

1-benzyl 2-tert-butyl (2S)-5-methoxypyrrolidine-1,2-dicarboxylate

1-benzyl 2-tert-butyl (2S,5R)-5-methylpyrrolidine-1,2-dicarboxylate

Downstream raw materials:

(5R,6S)-5,6-bis(4-chlorophenyl)-2-[((2S,5R)-2-{[(3S)-3,4-dimethylpiperazin-1-yl]carbonyl}-5-methylpyrrolidin-1-yl)carbonyl]-3-isopropyl-6-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole

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