(R)-2-(3-chloro-propyl)-N-((1S,2S)-1-hydroxy-1-phenyl-propan-2-yl)-N-methyl-pent-4-enamide

Base Information

• Chemical Name: (R)-2-(3-chloro-propyl)-N-((1S,2S)-1-hydroxy-1-phenyl-propan-2-yl)-N-methyl-pent-4-enamide
• CAS No.: 1013937-77-3
• Molecular Formula: C₁₈H₂₆ClNO₂
• Molecular Weight: 323.863
• Mol file: 1013937-77-3.mol

Synonyms:(R)-2-(3-chloro-propyl)-N-((1S,2S)-1-hydroxy-1-phenyl-propan-2-yl)-N-methyl-pent-4-enamide

Chemical Property of (R)-2-(3-chloro-propyl)-N-((1S,2S)-1-hydroxy-1-phenyl-propan-2-yl)-N-methyl-pent-4-enamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-(3-chloro-propyl)-N-((1S,2S)-1-hydroxy-1-phenyl-propan-2-yl)-N-methyl-pent-4-enamide

There total 2 articles about (R)-2-(3-chloro-propyl)-N-((1S,2S)-1-hydroxy-1-phenyl-propan-2-yl)-N-methyl-pent-4-enamide 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: 95.0%

5-chloro-N-((1S,2S)-1-hydroxy-1-phenyl-propan-2-yl)-N-methyl-pentanamide (1013937-76-2) + allyl bromide (106-95-6) → (R)-2-(3-chloro-propyl)-N-((1S,2S)-1-hydroxy-1-phenyl-propan-2-yl)-N-methyl-pent-4-enamide (1013937-77-3)

Guidance literature:

5-chloro-N-((1S,2S)-1-hydroxy-1-phenyl-propan-2-yl)-N-methyl-pentanamide; With n-butyllithium; diisopropylamine; lithium chloride; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 3h;

allyl bromide; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 0.866667h;

Reference yield:

5-Chlorovaleroyl chloride (1575-61-7) + pseudoephedrine (90-82-4,7009-81-6,90-83-5,6912-63-6) → (R)-2-(3-chloro-propyl)-N-((1S,2S)-1-hydroxy-1-phenyl-propan-2-yl)-N-methyl-pent-4-enamide (1013937-77-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / tetrahydrofuran / 1.25 h / 0 - 20 °C

2.1: n-butyllithium; diisopropylamine; lithium chloride / tetrahydrofuran; hexane / 3 h / -78 - 0 °C

2.2: 0.87 h / 0 - 20 °C

With n-butyllithium; triethylamine; diisopropylamine; lithium chloride; In tetrahydrofuran; hexane;

Reference yield:

(R)-2-(3-chloro-propyl)-N-((1S,2S)-1-hydroxy-1-phenyl-propan-2-yl)-N-methyl-pent-4-enamide (1013937-77-3) → methyl {2-[((R)-(3-chlorophenyl){3-[({(2S)-2-(methylamino)-3-[(3R)-tetrahydro-2H-pyran-3-yl]propyl}amino)carbonyl]phenyl}methyl)oxy]ethyl}carbamate hydrochloride

Guidance literature:

Multi-step reaction with 8 steps

1.1: n-butyllithium; borane-ammonia complex; diisopropylamine / tetrahydrofuran; hexane / 4.08 h / -78 - 20 °C

1.2: -10 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 2.92 h / 5 - 20 °C

3.1: ruthenium trichloride / water; acetonitrile / 0.08 h / 20 °C

3.2: 0.5 h / 20 °C

4.1: tetrahydrofuran / 1 h / 20 °C / Molecular sieve

5.1: 3-{(E)-[((1R,2R)-2-{[({(1S)-1-[(dimethylamino)carbonyl]-2,2-dimethylpropyl}amino)carbonothioyl]amino}cyclohexyl)imino]methyl}-5-(1,1-dimethylethyl)-4-hydroxyphenyl 2,2-dimethylpropanoate / toluene / 0.25 h / -78 °C

5.2: 4.17 h / -78 - 20 °C

6.1: ammonia; hydrogen / nickel / methanol / 0.5 h / 14 - 25 °C / 22801.5 Torr

7.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h

8.1: hydrogenchloride / 1,4-dioxane; acetonitrile

With hydrogenchloride; n-butyllithium; borane-ammonia complex; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; ammonia; hydrogen; sodium hydride; diisopropylamine; N-ethyl-N,N-diisopropylamine; ruthenium trichloride; 3-{(E)-[((1R,2R)-2-{[({(1S)-1-[(dimethylamino)carbonyl]-2,2-dimethylpropyl}amino)carbonothioyl]amino}cyclohexyl)imino]methyl}-5-(1,1-dimethylethyl)-4-hydroxyphenyl 2,2-dimethylpropanoate; nickel; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

5-chloro-N-((1S,2S)-1-hydroxy-1-phenyl-propan-2-yl)-N-methyl-pentanamide

allyl bromide

5-Chlorovaleroyl chloride

pseudoephedrine

Downstream raw materials:

tert-butyl (S)-1-amino-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl(methyl)carbamate

methyl {2-[((R)-(3-chlorophenyl){3-[({(2S)-2-(methylamino)-3-[(3R)-tetrahydro-2H-pyran-3-yl]propyl}amino)carbonyl]phenyl}methyl)oxy]ethyl}carbamate

methyl 2-((S)-(3-chloro-5-fluorophenyl)(3-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)phenyl)methoxy)ethylcarbamate

methyl 2-((R)-(3-chloro-5-fluorophenyl)(3-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)phenyl)methoxy)ethylcarbamate