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

Base Information

• Chemical Name: (5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-(hydroxymethyl)-N,N-dimethyl-L-prolinamide
• CAS No.: 1070868-58-4
• Molecular Formula: C₂₁H₂₅FN₂O₃
• Molecular Weight: 372.44
• Mol file: 1070868-58-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about (5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-(hydroxymethyl)-N,N-dimethyl-L-prolinamide 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: 49.4%

(5R)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-N,N-dimethyl-L-prolinamide (1070868-57-3) → (5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-(hydroxymethyl)-N,N-dimethyl-L-prolinamide (1070868-58-4)

Guidance literature:

(5R)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-N,N-dimethyl-L-prolinamide; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1h;

With sodium hydrogencarbonate; In tetrahydrofuran; water;

Reference yield:

o-fluorobenzyl bromide (446-48-0) → (5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-(hydroxymethyl)-N,N-dimethyl-L-prolinamide (1070868-58-4)

Guidance literature:

Multi-step reaction with 12 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

6.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.67 h / -78 - -40 °C

6.2: 7 h / -78 °C

7.1: 2,6-dimethylpyridine / dichloromethane / 3 h / 0 - 20 °C

8.1: lithium hydroxide / methanol; water / 2 h / 90 °C / Microwave irradiation

9.1: citric acid / water / pH 5

10.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 20 °C

11.1: hydrogen / palladium on activated carbon / methanol / 1 h / 20 °C / 760.05 Torr

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C

With 2,6-dimethylpyridine; lithium hydroxide; tetrabutyl ammonium fluoride; hydrogen; iodine; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; magnesium; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; citric acid; lithium hexamethyldisilazane; platinum on carbon; palladium on activated carbon; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone;

Reference yield:

1-[(4-bromophenoxy)methyl]-2-fluorobenzene (934240-59-2) → (5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-(hydroxymethyl)-N,N-dimethyl-L-prolinamide (1070868-58-4)

Guidance literature:

Multi-step reaction with 11 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 / 0.67 h / -78 - -40 °C

5.2: 7 h / -78 °C

6.1: 2,6-dimethylpyridine / dichloromethane / 3 h / 0 - 20 °C

7.1: lithium hydroxide / methanol; water / 2 h / 90 °C / Microwave irradiation

8.1: citric acid / water / pH 5

9.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 20 °C

10.1: hydrogen / palladium on activated carbon / methanol / 1 h / 20 °C / 760.05 Torr

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C

With 2,6-dimethylpyridine; lithium hydroxide; tetrabutyl ammonium fluoride; hydrogen; iodine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; magnesium; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; citric acid; lithium hexamethyldisilazane; platinum on carbon; palladium on activated carbon; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

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

o-fluorobenzyl bromide

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

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

Downstream raw materials:

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