Trifluoro-methanesulfonic acid (1R,4S)-2-(4-methoxy-benzyl)-3-oxo-2-aza-bicyclo[2.2.1]hept-5-en-6-yl ester

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (1R,4S)-2-(4-methoxy-benzyl)-3-oxo-2-aza-bicyclo[2.2.1]hept-5-en-6-yl ester
• CAS No.: 168773-58-8
• Molecular Formula: C₁₅H₁₄F₃NO₅S
• Molecular Weight: 377.341
• Mol file: 168773-58-8.mol

Synonyms:Trifluoro-methanesulfonic acid (1R,4S)-2-(4-methoxy-benzyl)-3-oxo-2-aza-bicyclo[2.2.1]hept-5-en-6-yl ester

Chemical Property of Trifluoro-methanesulfonic acid (1R,4S)-2-(4-methoxy-benzyl)-3-oxo-2-aza-bicyclo[2.2.1]hept-5-en-6-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Trifluoro-methanesulfonic acid (1R,4S)-2-(4-methoxy-benzyl)-3-oxo-2-aza-bicyclo[2.2.1]hept-5-en-6-yl ester

There total 18 articles about Trifluoro-methanesulfonic acid (1R,4S)-2-(4-methoxy-benzyl)-3-oxo-2-aza-bicyclo[2.2.1]hept-5-en-6-yl 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: 40.0%

1,1,1-trifluoro-N-(pyridin-2-yl)-N-((trifluoromethyl)sulfonyl)methane sulfonamide (145100-50-1) + (1R,4S)-2-(p-Methoxybenzyl)-2-azabicylo<2.2.1>heptane-3,6-dione (168773-57-7) → Trifluoro-methanesulfonic acid (1R,4S)-2-(4-methoxy-benzyl)-3-oxo-2-aza-bicyclo[2.2.1]hept-5-en-6-yl ester (168773-58-8)

Guidance literature:

With lithium hexamethyldisilazane;

DOI:10.1021/jo00119a044

Reference yield: 20.0%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + (1R,4S)-2-(p-Methoxybenzyl)-2-azabicylo<2.2.1>heptane-3,6-dione (168773-57-7) → Trifluoro-methanesulfonic acid (1R,4S)-2-(4-methoxy-benzyl)-3-oxo-2-aza-bicyclo[2.2.1]hept-5-en-6-yl ester (168773-58-8)

Guidance literature:

DOI:10.1021/jo00119a044

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → Trifluoro-methanesulfonic acid (1R,4S)-2-(4-methoxy-benzyl)-3-oxo-2-aza-bicyclo[2.2.1]hept-5-en-6-yl ester (168773-58-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h

2: 97 percent / TBAF / tetrahydrofuran / 0.33 h

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min

4: 20 percent

With oxalyl dichloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran;

DOI:10.1021/jo00119a044

upstream raw materials:

N,N-phenylbistrifluoromethane-sulfonimide

(1R,4S)-2-(p-Methoxybenzyl)-2-azabicylo<2.2.1>heptane-3,6-dione

1,1,1-trifluoro-N-(pyridin-2-yl)-N-((trifluoromethyl)sulfonyl)methane sulfonamide

p-Methoxybenzyl bromide

Downstream raw materials:

(-)-2-azabicyclo[2.2.1]hept-5-en-3-one

(1R,4S)-N-(tert-Butyloxycarbonyl)-1-amino-4-(hydroxymethyl)-2-cyclopentene

tert-butyl (1R,4S)-(-)-3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate

(1R,4S)-2-(p-Methoxybenzyl)-2-azabicyclo<2.2.1>-5-hepten-3-one