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

Base Information

• Chemical Name: (5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-(hydroxymethyl)-N,N-dimethyl-L-prolinamide hydrochloride
• CAS No.: 1070868-64-2
• Molecular Formula: C₂₁H₂₅FN₂O₃*ClH
• Molecular Weight: 408.9
• Mol file: 1070868-64-2.mol

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

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

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 hydrochloride

There total 15 articles about (5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-(hydroxymethyl)-N,N-dimethyl-L-prolinamide hydrochloride 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: 48.3%

(5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-(hydroxymethyl)-N,N-dimethyl-L-prolinamide (1070868-58-4) → (5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-(hydroxymethyl)-N,N-dimethyl-L-prolinamide hydrochloride (1070868-64-2)

Guidance literature:

With hydrogenchloride; In diethyl ether;

Reference yield:

o-fluorobenzyl bromide (446-48-0) → (5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-(hydroxymethyl)-N,N-dimethyl-L-prolinamide hydrochloride (1070868-64-2)

Guidance literature:

Multi-step reaction with 13 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

13.1: hydrogenchloride / diethyl ether

With 2,6-dimethylpyridine; hydrogenchloride; 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; diethyl ether; 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 hydrochloride (1070868-64-2)

Guidance literature:

Multi-step reaction with 12 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

12.1: hydrogenchloride / diethyl ether

With 2,6-dimethylpyridine; hydrogenchloride; 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; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

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