Methanesulfonic acid, trifluoro-, (3S,4S)-1-cyclohexyl-3,4-pyrrolidinediyl ester

Base Information

• Chemical Name: Methanesulfonic acid, trifluoro-, (3S,4S)-1-cyclohexyl-3,4-pyrrolidinediyl ester
• CAS No.: 209625-82-1
• Molecular Formula: C12H17F6NO6S2
• Molecular Weight: 449.392
• Mol file: 209625-82-1.mol

Synonyms:

Chemical Property of Methanesulfonic acid, trifluoro-, (3S,4S)-1-cyclohexyl-3,4-pyrrolidinediyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid, trifluoro-, (3S,4S)-1-cyclohexyl-3,4-pyrrolidinediyl ester

There total 5 articles about Methanesulfonic acid, trifluoro-, (3S,4S)-1-cyclohexyl-3,4-pyrrolidinediyl ester 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:

trifluoromethylsulfonic anhydride (358-23-6) + (3S,4S)-1-cyclohexylpyrrolidine-3,4-diol (90304-05-5) → (3S,4S)-1-cyclohexyl-3,4-bis(trifluoromethanesulfonyloxy)pyrrolidine (209625-82-1)

Guidance literature:

With pyridine; at -80 ℃; for 4h;

DOI:10.1039/a801718b

Reference yield:

(3R,4R)-1-cyclohexyl-3,4-diacetoxypyrrolidine-2,5-dione (209625-83-2) → (3S,4S)-1-cyclohexyl-3,4-bis(trifluoromethanesulfonyloxy)pyrrolidine (209625-82-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 34 percent / sodium borohydride; iodine / tetrahydrofuran / Heating

2: triethylamine / CH₂Cl₂ / 16 h / 20 °C

With sodium tetrahydroborate; iodine; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo0513414

Reference yield:

cyclohexylamine (108-91-8,157973-60-9) → (3S,4S)-1-cyclohexyl-3,4-bis(trifluoromethanesulfonyloxy)pyrrolidine (209625-82-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 2.) SOCl₂ / 1.) 20 deg C, 12 h, 2.) 20 deg C, 24 h

2: NaBH₄, I₂ / tetrahydrofuran / 12 h

3: AcOH, HCl / 10 h

4: pyridine / 4 h / -80 °C

With pyridine; hydrogenchloride; sodium tetrahydroborate; thionyl chloride; iodine; acetic acid; In tetrahydrofuran;

DOI:10.1039/a801718b

upstream raw materials:

trifluoromethylsulfonic anhydride

(3S,4S)-1-cyclohexylpyrrolidine-3,4-diol

cyclohexylamine

(3R,4R)-1-cyclohexyl-3,4-diacetoxypyrrolidine-2,5-dione

Downstream raw materials:

(3R,4R)-1-cyclohexyl-3,4-difluoropyrrolidine