(3S,4S)-1-benzylpyrrolidine-3,4-diyl bis(trifluoromethanesulfonate)

Base Information

• Chemical Name: (3S,4S)-1-benzylpyrrolidine-3,4-diyl bis(trifluoromethanesulfonate)
• CAS No.: 219317-52-9
• Molecular Formula: C₁₃H₁₃F₆NO₆S₂
• Molecular Weight: 457.372
• Mol file: 219317-52-9.mol

Synonyms:(3S,4S)-1-benzylpyrrolidine-3,4-diyl bis(trifluoromethanesulfonate)

Chemical Property of (3S,4S)-1-benzylpyrrolidine-3,4-diyl bis(trifluoromethanesulfonate)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-1-benzylpyrrolidine-3,4-diyl bis(trifluoromethanesulfonate)

There total 3 articles about (3S,4S)-1-benzylpyrrolidine-3,4-diyl bis(trifluoromethanesulfonate) 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: 79.0%

trifluoromethylsulfonic anhydride (358-23-6) + (3S,4S)-(+)-1-benzyl-3,4-pyrrolidinediol (90365-74-5,330152-66-4) → (3S,4S)-1-benzylpyrrolidine-3,4-diyl bis(trifluoromethanesulfonate) (219317-52-9)

Guidance literature:

With pyridine; In dichloromethane; at -40 - 20 ℃;

DOI:10.1021/acs.jmedchem.6b01163

Reference yield:

benzylamine (100-46-9) → (3S,4S)-1-benzylpyrrolidine-3,4-diyl bis(trifluoromethanesulfonate) (219317-52-9)

Guidance literature:

Multi-step reaction with 3 steps

1: o-xylene / 4 h / Dean-Stark; Reflux

2: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux

3: pyridine / dichloromethane / -40 - 20 °C

With pyridine; lithium aluminium tetrahydride; In tetrahydrofuran; dichloromethane; o-xylene;

DOI:10.1021/acs.jmedchem.6b01163

Reference yield:

(3R,4R)-1-benzyl-3,4-dihydroxypyrrolidine-2,5-dione (75172-31-5) → (3S,4S)-1-benzylpyrrolidine-3,4-diyl bis(trifluoromethanesulfonate) (219317-52-9)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux

2: pyridine / dichloromethane / -40 - 20 °C

With pyridine; lithium aluminium tetrahydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/acs.jmedchem.6b01163

upstream raw materials:

trifluoromethylsulfonic anhydride

(3S,4S)-(+)-1-benzyl-3,4-pyrrolidinediol

benzylamine

(3R,4R)-1-benzyl-3,4-dihydroxypyrrolidine-2,5-dione

Downstream raw materials:

(R,R)-1-benzyl-3,4-bis(isopropylsulfanyl)pyrrolidine

(+)-(3R,4R)-1-benzyl-3,4-bis(phenylsulfanyl)pyrrolidine

(R,R)-1-benzyl-3,4-bis(methylsulfanyl)pyrrolidine