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

Base Information

• Chemical Name: 2-methyl 1-(phenylmethyl) (2S,5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-1,2-pyrrolidinedicarboxylate
• CAS No.: 934585-16-7
• Molecular Formula: C₂₇H₂₆FNO₅
• Molecular Weight: 463.506
• Mol file: 934585-16-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about 2-methyl 1-(phenylmethyl) (2S,5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-1,2-pyrrolidinedicarboxylate 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: 97.0%

(2S,5R)-methyl-5-(4-((2-fluorobenzyl)oxy)phenyl)pyrrolidine-2-carboxylate (934240-62-7) + benzyl chloroformate (501-53-1,94274-21-2) → 2-methyl 1-(phenylmethyl) (2S,5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-1,2-pyrrolidinedicarboxylate (934585-16-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 1h;

Reference yield:

o-fluorobenzyl bromide (446-48-0) → 2-methyl 1-(phenylmethyl) (2S,5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-1,2-pyrrolidinedicarboxylate (934585-16-7)

Guidance literature:

Multi-step reaction with 5 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

4.1: hydrogen / platinum on carbon / ethyl acetate / 1.5 h / 1520.1 Torr

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 - 20 °C

With hydrogen; iodine; potassium carbonate; magnesium; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; platinum on carbon; In tetrahydrofuran; dichloromethane; ethyl acetate; acetone;

Reference yield:

methyl (S)-5-(4-((2-fluorobenzyl)oxy)phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate (934240-61-6) → 2-methyl 1-(phenylmethyl) (2S,5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-1,2-pyrrolidinedicarboxylate (934585-16-7)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen / platinum on carbon / ethyl acetate / 1.5 h / 1520.1 Torr

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 - 20 °C

With hydrogen; N-ethyl-N,N-diisopropylamine; platinum on carbon; In dichloromethane; ethyl acetate;

upstream raw materials:

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

benzyl chloroformate

o-fluorobenzyl bromide

1-[(4-bromophenoxy)methyl]-2-fluorobenzene

Downstream raw materials:

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

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