methyl (S)-5-(4-((2-fluorobenzyl)oxy)phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

Base Information

• Chemical Name: methyl (S)-5-(4-((2-fluorobenzyl)oxy)phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate
• CAS No.: 934240-61-6
• Molecular Formula: C₁₉H₁₈FNO₃
• Molecular Weight: 327.355
• Mol file: 934240-61-6.mol

Synonyms:methyl (S)-5-(4-((2-fluorobenzyl)oxy)phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

Chemical Property of methyl (S)-5-(4-((2-fluorobenzyl)oxy)phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (S)-5-(4-((2-fluorobenzyl)oxy)phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

There total 8 articles about methyl (S)-5-(4-((2-fluorobenzyl)oxy)phenyl)-3,4-dihydro-2H-pyrrole-2-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: 78.0%

methyl (S)-2-((tert-butoxycarbonyl)amino)-5-(4-((2-fluorobenzyl)oxy)phenyl)-5-oxopentanoate (934240-60-5) → methyl (S)-5-(4-((2-fluorobenzyl)oxy)phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate (934240-61-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 5 - 30 ℃; for 4h; Inert atmosphere; Large scale;

DOI:10.1021/acs.oprd.0c00382

Reference yield: 68.0%

tert-butyl (S)-4-(3-(4-((2-fluorobenzyl)oxy)phenyl)-3-oxopropyl)-5-oxooxazolidine-3-carboxylate → methyl (S)-5-(4-((2-fluorobenzyl)oxy)phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate (934240-61-6)

Guidance literature:

With methanesulfonic acid; In tetrahydrofuran; methanol; at 20 ℃; for 14h;

Reference yield:

o-fluorobenzyl bromide (446-48-0) → methyl (S)-5-(4-((2-fluorobenzyl)oxy)phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate (934240-61-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / acetone / 2 h / Heating / reflux

2.1: iodine; magnesium / tetrahydrofuran / 1 h / 20 - 65 °C / Heating / reflux

2.2: 2.25 h / -60 °C

3.1: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C

With iodine; potassium carbonate; magnesium; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; acetone;

upstream raw materials:

methyl (S)-2-((tert-butoxycarbonyl)amino)-5-(4-((2-fluorobenzyl)oxy)phenyl)-5-oxopentanoate

o-fluorobenzyl bromide

4-bromo-phenol

(4-((2-fluorobenzyl)oxy)phenyl)boronic acid

Downstream raw materials:

(2S,5R)-methyl-5-(4-((2-fluorobenzyl)oxy)phenyl)pyrrolidine-2-carboxylate

2-methyl 1-(phenylmethyl) (2S,5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-1,2-pyrrolidinedicarboxylate

2-methyl 1-(phenylmethyl) (2R,5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-(hydroxymethyl)-1,2-pyrrolidinedicarboxylate

(5R)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-1-{[(phenylmethyl)oxy]carbonyl}-L-proline