2-cyclopropyl-N-[(3R)-3-hydroxy-4,4-dimethyl-pentyl]-6-methyl-4-morpholin-4-yl-benzamide

Base Information

• Chemical Name: 2-cyclopropyl-N-[(3R)-3-hydroxy-4,4-dimethyl-pentyl]-6-methyl-4-morpholin-4-yl-benzamide
• CAS No.: 1472103-93-7
• Molecular Formula: C₂₂H₃₄N₂O₃
• Molecular Weight: 374.524
• Mol file: 1472103-93-7.mol

Synonyms:2-cyclopropyl-N-[(3R)-3-hydroxy-4,4-dimethyl-pentyl]-6-methyl-4-morpholin-4-yl-benzamide

Chemical Property of 2-cyclopropyl-N-[(3R)-3-hydroxy-4,4-dimethyl-pentyl]-6-methyl-4-morpholin-4-yl-benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-cyclopropyl-N-[(3R)-3-hydroxy-4,4-dimethyl-pentyl]-6-methyl-4-morpholin-4-yl-benzamide

There total 16 articles about 2-cyclopropyl-N-[(3R)-3-hydroxy-4,4-dimethyl-pentyl]-6-methyl-4-morpholin-4-yl-benzamide 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: 39.0%

(3R)-1-amino-4,4-dimethyl-pentan-3-ol (858130-55-9,552338-18-8) + 2-cyclopropyl-6-methyl-4-morpholin-4-yl-benzoic acid (1472104-42-9) → 2-cyclopropyl-N-[(3R)-3-hydroxy-4,4-dimethyl-pentyl]-6-methyl-4-morpholin-4-yl-benzamide (1472103-93-7)

Guidance literature:

2-cyclopropyl-6-methyl-4-morpholin-4-yl-benzoic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.25h;

(3R)-1-amino-4,4-dimethyl-pentan-3-ol; In dichloromethane; at 23 ℃; for 16h;

Reference yield:

(4-Bromo-2-methoxy-6-methyl-phenyl)-amine hydrobromide (1181458-21-8) → 2-cyclopropyl-N-[(3R)-3-hydroxy-4,4-dimethyl-pentyl]-6-methyl-4-morpholin-4-yl-benzamide (1472103-93-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C

1.2: 4 h / 0 - 50 °C

2.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 18 h / -78 - 23 °C

2.2: 1 h / 0 - 23 °C

3.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 0.5 h / 23 °C

4.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 23 °C

5.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 16.5 h / 120 °C / Inert atmosphere

6.1: boron tribromide / dichloromethane / 1.5 h / -78 - 23 °C

6.2: Cooling

7.1: caesium carbonate / dichloromethane; acetonitrile / 2 h / 23 °C

8.1: potassium fluoride; potassium bromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 1.33 h / 120 °C / Inert atmosphere; Microwave irradiation

9.1: potassium hydroxide; ethylene glycol / 16 h / 150 - 160 °C

10.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 0 °C

10.2: 16 h / 23 °C

With hydrogenchloride; potassium fluoride; sodium chlorite; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium dihydrogenphosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2-methyl-but-2-ene; boron tribromide; diisobutylaluminium hydride; potassium carbonate; benzotriazol-1-ol; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; ethylene glycol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; potassium bromide; potassium hydroxide; sodium nitrite; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

Reference yield:

4-bromo-2-methoxy-6-methyl-benzonitrile (877149-05-8) → 2-cyclopropyl-N-[(3R)-3-hydroxy-4,4-dimethyl-pentyl]-6-methyl-4-morpholin-4-yl-benzamide (1472103-93-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 18 h / -78 - 23 °C

1.2: 1 h / 0 - 23 °C

2.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 0.5 h / 23 °C

3.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 23 °C

4.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 16.5 h / 120 °C / Inert atmosphere

5.1: boron tribromide / dichloromethane / 1.5 h / -78 - 23 °C

5.2: Cooling

6.1: caesium carbonate / dichloromethane; acetonitrile / 2 h / 23 °C

7.1: potassium fluoride; potassium bromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 1.33 h / 120 °C / Inert atmosphere; Microwave irradiation

8.1: potassium hydroxide; ethylene glycol / 16 h / 150 - 160 °C

9.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 0 °C

9.2: 16 h / 23 °C

With potassium fluoride; sodium chlorite; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium dihydrogenphosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2-methyl-but-2-ene; boron tribromide; diisobutylaluminium hydride; potassium carbonate; benzotriazol-1-ol; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; ethylene glycol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; potassium bromide; potassium hydroxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

upstream raw materials:

(4-Bromo-2-methoxy-6-methyl-phenyl)-amine hydrobromide

4-bromo-2-methoxy-6-methyl-benzonitrile

4-bromo-2-methoxy-6-methyl-benzaldehyde

4-bromo-2-methoxy-6-methyl-benzoic acid