(-)-tert-butyl (S)-4-benzyl-3-[(S)-1-(pyrrolidin-1-yl)ethyl]piperazine-1-carboxylate

Base Information

• Chemical Name: (-)-tert-butyl (S)-4-benzyl-3-[(S)-1-(pyrrolidin-1-yl)ethyl]piperazine-1-carboxylate
• CAS No.: 361568-84-5
• Molecular Formula: C₂₂H₃₅N₃O₂
• Molecular Weight: 373.539
• Mol file: 361568-84-5.mol

Synonyms:(-)-tert-butyl (S)-4-benzyl-3-[(S)-1-(pyrrolidin-1-yl)ethyl]piperazine-1-carboxylate

Chemical Property of (-)-tert-butyl (S)-4-benzyl-3-[(S)-1-(pyrrolidin-1-yl)ethyl]piperazine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-tert-butyl (S)-4-benzyl-3-[(S)-1-(pyrrolidin-1-yl)ethyl]piperazine-1-carboxylate

There total 2 articles about (-)-tert-butyl (S)-4-benzyl-3-[(S)-1-(pyrrolidin-1-yl)ethyl]piperazine-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: 54.0%

pyrrolidine (123-75-1) + (-)-tert-butyl (S)-3-acetyl-4-benzylpiperazine-1-carboxylate (361568-78-7) → (-)-tert-butyl (S)-4-benzyl-3-[(S)-1-(pyrrolidin-1-yl)ethyl]piperazine-1-carboxylate (361568-84-5) + (-)-tert-butyl (S)-4-benzyl-3-[(R)-1-(pyrrolidin-1-yl)ethyl]piperazine-1-carboxylate (361568-82-3)

Guidance literature:

pyrrolidine; (-)-tert-butyl (S)-3-acetyl-4-benzylpiperazine-1-carboxylate; With titanium(IV) isopropylate; In dichloromethane; at 20 ℃; for 1.5h;

With 3 A molecular sieve; sodium cyanoborohydride; In methanol; dichloromethane; at 20 ℃; for 40h; Further stages.;

DOI:10.1021/jm0108395

Reference yield:

(S)-4-Benzyl-3-((S)-1-hydroxy-ethyl)-piperazine-1-carboxylic acid tert-butyl ester → (-)-tert-butyl (S)-4-benzyl-3-[(S)-1-(pyrrolidin-1-yl)ethyl]piperazine-1-carboxylate (361568-84-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 82 percent / N-methylmorpholine N-oxide; tetrapropylammonium perrutenate; 4 Angstroem sieves / CH₂Cl₂ / 16 h / 20 °C

2.1: Ti(OiPr)4 / CH₂Cl₂ / 1.5 h / 20 °C

2.2: 21 percent / NaBH₃CN; 3 Angstroem sieves / methanol; CH₂Cl₂ / 40 h / 20 °C

With titanium(IV) isopropylate; tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide; In dichloromethane;

DOI:10.1021/jm0108395

Reference yield:

(-)-tert-butyl (S)-4-benzyl-3-[(S)-1-(pyrrolidin-1-yl)ethyl]piperazine-1-carboxylate (361568-84-5) → (+)-tert-butyl (S)-4-[2-(3,4-dichlorophenyl)acetyl]-3-[(S)-1-(pyrrolidin-1-yl)ethyl]piperazine-1-carboxylate (361568-92-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 279 mg / H₂ / 10percent Pd/C / methanol / 9 h / 20 °C / 975.1 Torr

2.1: 1,1'-carbonyldiimidazole / CH₂Cl₂ / 2 h / 20 °C

2.2: 59 percent / CH₂Cl₂ / 24 h / 20 °C

With hydrogen; 1,1'-carbonyldiimidazole; 10percent Pd/C; In methanol; dichloromethane;

DOI:10.1021/jm0108395

upstream raw materials:

pyrrolidine

(-)-tert-butyl (S)-3-acetyl-4-benzylpiperazine-1-carboxylate

Downstream raw materials:

(+)-tert-butyl (S)-4-[2-(3,4-dichlorophenyl)acetyl]-3-[(S)-1-(pyrrolidin-1-yl)ethyl]piperazine-1-carboxylate