(1S,2R)-[1-(3,5-difluorobenzyl)-2-hydroxy-3-(3-methoxybenzylamino)propyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: (1S,2R)-[1-(3,5-difluorobenzyl)-2-hydroxy-3-(3-methoxybenzylamino)propyl]-carbamic acid tert-butyl ester
• CAS No.: 388071-80-5
• Molecular Formula: C₂₃H₃₀F₂N₂O₄
• Molecular Weight: 436.499
• Mol file: 388071-80-5.mol

Synonyms:(1S,2R)-[1-(3,5-difluorobenzyl)-2-hydroxy-3-(3-methoxybenzylamino)propyl]-carbamic acid tert-butyl ester

Chemical Property of (1S,2R)-[1-(3,5-difluorobenzyl)-2-hydroxy-3-(3-methoxybenzylamino)propyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R)-[1-(3,5-difluorobenzyl)-2-hydroxy-3-(3-methoxybenzylamino)propyl]-carbamic acid tert-butyl ester

There total 18 articles about (1S,2R)-[1-(3,5-difluorobenzyl)-2-hydroxy-3-(3-methoxybenzylamino)propyl]-carbamic acid tert-butyl ester 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: 69.0%

tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate (388071-27-0) + 3-METHOXYBENZYLAMINE (5071-96-5) → (1S,2R)-[1-(3,5-difluorobenzyl)-2-hydroxy-3-(3-methoxybenzylamino)propyl]-carbamic acid tert-butyl ester (388071-80-5)

Guidance literature:

In isopropyl alcohol; at 80 ℃; for 20h; Inert atmosphere;

DOI:10.1016/j.tetlet.2017.09.025

Reference yield:

3-(3,5-difluorophenyl)propionic acid (84315-24-2) → (1S,2R)-[1-(3,5-difluorobenzyl)-2-hydroxy-3-(3-methoxybenzylamino)propyl]-carbamic acid tert-butyl ester (388071-80-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: triethylamine / diethyl ether / -78 - 0 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C / Inert atmosphere

2.2: -78 - 0 °C / Inert atmosphere

3.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 23 °C / Inert atmosphere

3.2: 2.5 h / -78 - 23 °C / Inert atmosphere

4.1: water; dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran / 0 - 23 °C / Inert atmosphere

4.2: 16 h / 90 °C / Inert atmosphere

5.1: water; potassium hydroxide / ethanol / 4 h / 70 °C / Inert atmosphere

5.2: 23 °C / pH 7 / Inert atmosphere

6.1: dichloromethane; water; ethanol / 4 h / 23 °C / Inert atmosphere

7.1: hydrogen; palladium hydroxide 10 wt. % on activated carbon / ethyl acetate / 24 h / 23 °C

8.1: triethylamine; di(n-butyl)tin oxide / dichloromethane / 4 h / 23 °C / Inert atmosphere

9.1: potassium carbonate / methanol / 0 - 23 °C / Inert atmosphere

10.1: isopropyl alcohol / 20 h / 80 °C / Inert atmosphere

With n-butyllithium; lithium hydroxide monohydrate; di-n-butylboryl trifluoromethanesulfonate; palladium hydroxide 10 wt. % on activated carbon; water; hydrogen; dihydrogen peroxide; di(n-butyl)tin oxide; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; ethyl acetate; isopropyl alcohol; 3.1: |Evans Aldol Reaction / 3.2: |Evans Aldol Reaction / 4.2: |Curtius Rearrangement;

DOI:10.1016/j.tetlet.2017.09.025

Reference yield:

C14H16F2O3 → (1S,2R)-[1-(3,5-difluorobenzyl)-2-hydroxy-3-(3-methoxybenzylamino)propyl]-carbamic acid tert-butyl ester (388071-80-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C / Inert atmosphere

1.2: -78 - 0 °C / Inert atmosphere

2.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 23 °C / Inert atmosphere

2.2: 2.5 h / -78 - 23 °C / Inert atmosphere

3.1: lithium hydroxide; water; dihydrogen peroxide / tetrahydrofuran / 12 h / 25 °C / Inert atmosphere

3.2: pH Ca_. 1 / Acidic conditions

4.1: triethylamine; diphenyl phosphoryl azide / benzine / 12 h / 90 °C / Inert atmosphere

5.1: ozone / methanol; dichloromethane / -78 °C

5.2: -78 - 23 °C

6.1: water; potassium hydroxide / ethanol / 4 h / 70 °C / Inert atmosphere

7.1: dichloromethane / 8 h / 23 °C / Inert atmosphere

8.1: triethylamine; di(n-butyl)tin oxide / dichloromethane / 4 h / 23 °C / Inert atmosphere

9.1: potassium carbonate / methanol / 0 - 23 °C / Inert atmosphere

10.1: isopropyl alcohol / 20 h / 80 °C / Inert atmosphere

With n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; diphenyl phosphoryl azide; water; dihydrogen peroxide; di(n-butyl)tin oxide; potassium carbonate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hydroxide; lithium hydroxide; In tetrahydrofuran; methanol; benzine; ethanol; hexane; dichloromethane; isopropyl alcohol; 2.1: |Evans Aldol Reaction / 2.2: |Evans Aldol Reaction / 4.1: |Curtius Rearrangement;

DOI:10.1016/j.tetlet.2017.09.025

upstream raw materials:

tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate

3-METHOXYBENZYLAMINE

3-(3,5-difluorophenyl)propionic acid

tert-butyl [(2S,3S)-1-(3,5-difluorophenyl)-3,4-dihydroxybutan-2-yl]carbamate

Downstream raw materials:

[3-tert-butoxycarbonylamino-4-(3,5-difluoro-phenyl)-2-hydroxy-butyl]-(3-methoxybenzyl)-carbamic acid benzyl ester

(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol trifluoroacetate

(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]butan-2-ol