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

Base Information

• Chemical Name: phenylmethyl (2R,5R)-2-[(dimethylamino)carbonyl]-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-[(methyloxy)methyl]-1-pyrrolidinecarboxylate
• CAS No.: 1070868-53-9
• Molecular Formula: C₃₀H₃₃FN₂O₅
• Molecular Weight: 520.601
• Mol file: 1070868-53-9.mol

Synonyms:phenylmethyl (2R,5R)-2-[(dimethylamino)carbonyl]-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-[(methyloxy)methyl]-1-pyrrolidinecarboxylate

Chemical Property of phenylmethyl (2R,5R)-2-[(dimethylamino)carbonyl]-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-[(methyloxy)methyl]-1-pyrrolidinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenylmethyl (2R,5R)-2-[(dimethylamino)carbonyl]-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-[(methyloxy)methyl]-1-pyrrolidinecarboxylate

There total 9 articles about phenylmethyl (2R,5R)-2-[(dimethylamino)carbonyl]-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-[(methyloxy)methyl]-1-pyrrolidinecarboxylate 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: 85.0%

(5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-[(methyloxy)methyl]-1-{[(phenylmethyl)oxy]carbonyl}-L-proline (1070868-45-9) + dimethyl amine (124-40-3) → phenylmethyl (2R,5R)-2-[(dimethylamino)carbonyl]-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-[(methyloxy)methyl]-1-pyrrolidinecarboxylate (1070868-53-9)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In tert-Amyl alcohol; N,N-dimethyl-formamide; at 20 ℃; for 1h;

Reference yield:

1-[(4-bromophenoxy)methyl]-2-fluorobenzene (934240-59-2) → phenylmethyl (2R,5R)-2-[(dimethylamino)carbonyl]-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-[(methyloxy)methyl]-1-pyrrolidinecarboxylate (1070868-53-9)

Guidance literature:

Multi-step reaction with 7 steps

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

1.2: 2.25 h / -60 °C

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

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

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

5.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - -40 °C

5.2: 3 h / -78 °C

6.1: lithium hydroxide / methanol; water / 1 h / 80 °C / Microwave irradiation

6.2: pH 5 / Aqueous citrate buffer

7.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tert-Amyl alcohol; N,N-dimethyl-formamide / 1 h / 20 °C

With lithium hydroxide; hydrogen; iodine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; magnesium; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hexamethyldisilazane; platinum on carbon; In tetrahydrofuran; methanol; tert-Amyl alcohol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

methyl (S)-5-(4-((2-fluorobenzyl)oxy)phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate (934240-61-6) → phenylmethyl (2R,5R)-2-[(dimethylamino)carbonyl]-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-[(methyloxy)methyl]-1-pyrrolidinecarboxylate (1070868-53-9)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - -40 °C

3.2: 3 h / -78 °C

4.1: lithium hydroxide / methanol; water / 1 h / 80 °C / Microwave irradiation

4.2: pH 5 / Aqueous citrate buffer

5.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tert-Amyl alcohol; N,N-dimethyl-formamide / 1 h / 20 °C

With lithium hydroxide; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; platinum on carbon; In tetrahydrofuran; methanol; tert-Amyl alcohol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

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

dimethyl amine

o-fluorobenzyl bromide

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

Downstream raw materials:

(5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-N,N-dimethyl-2-[(methyloxy)methyl]-L-prolinamide

(5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-N,N-dimethyl-2-[(methyloxy)methyl]-L-prolinamide hydrochloride