（2s，4s）-1-benzyl-2-methy-4-fluoropyrrolidine-1，2-dicarbo

Base Information

• Chemical Name: （2s，4s）-1-benzyl-2-methy-4-fluoropyrrolidine-1，2-dicarbo
• CAS No.: 72180-14-4
• Molecular Formula: C14H16FNO4
• Molecular Weight: 281.284
• Hs Code.: 2933990090
• Mol file: 72180-14-4.mol

Synonyms:1,2-Pyrrolidinedicarboxylicacid, 4-fluoro-, 2-methyl 1-(phenylmethyl) ester, (2S-cis)-;(2S,4S)-1-(Benzyloxycarbonyl)-2-(methoxycarbonyl)-4-fluoropyrrolidine;

Chemical Property of （2s，4s）-1-benzyl-2-methy-4-fluoropyrrolidine-1，2-dicarbo

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.538
• Boiling Point: 382.901 °C at 760 mmHg
• PKA: -5.73±0.60(Predicted)
• Flash Point: 185.372 °C
• PSA: 55.84000
• Density: 1.267 g/cm³
• LogP: 1.84650
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

(2S,4S)-1-Benzyl-2-methy-4-fluoropyrrolidine-1,2-dicarboxylate 91% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of （2s，4s）-1-benzyl-2-methy-4-fluoropyrrolidine-1，2-dicarbo

There total 5 articles about （2s，4s）-1-benzyl-2-methy-4-fluoropyrrolidine-1，2-dicarbo 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: 95.0%

methanol (67-56-1) + (2S,4S)-N-Cbz-4-fluoropyrrolidine-2-carbonyl fluoride (1235447-42-3) → N-<(phenylmethoxy)carbonyl>-4(S)-fluoro-(S)-proline methyl ester (72180-14-4)

Guidance literature:

In dichloromethane; at 20 ℃; for 1h;

Reference yield: 94.0%

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (64187-48-0) → N-<(phenylmethoxy)carbonyl>-4(S)-fluoro-(S)-proline methyl ester (72180-14-4)

Guidance literature:

With (bis-(2-methoxyethyl)amino)sulfur trufluoride; In dichloromethane; at -78 - 20 ℃;

Reference yield:

(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (13504-85-3) → N-<(phenylmethoxy)carbonyl>-4(S)-fluoro-(S)-proline methyl ester (72180-14-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride / dichloromethane / 61 h / 0 - 20 °C / Inert atmosphere

2: triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere

With 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride; triethylamine; In dichloromethane;

DOI:10.1021/jo1025783

upstream raw materials:

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

methanol

(2S,4S)-N-Cbz-4-fluoropyrrolidine-2-carbonyl fluoride

(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Downstream raw materials:

C₁₃H₁₄FNO₃

C₁₉H₂₂FN₃

C₂₁H₂₆FN₃

(2S,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid

Refernces

• 1、 Gichuhi, Paul N.,Kuriyama, Masami,Onomura, Osamu. "Diastereoselective synthesis of 3-fluoro-2-substituted piperidines and pyrrolidines". . p. 331 - 346. Retrieved 2014/01/17.
• 2、 Singh, Rajendra P.,Umemoto, Teruo. "4-fluoropyrrolidine-2-carbonyl fluorides: Useful synthons and their facile preparation with 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride". experimental part. p. 3113 - 3121. Retrieved 2011/06/21.