N-((2R,3R)-3-hydroxy-5-phenyl-1-(pyrrolidin-1-yl)pent-4-yn-2-yl)palmitamide

Base Information

• Chemical Name: N-((2R,3R)-3-hydroxy-5-phenyl-1-(pyrrolidin-1-yl)pent-4-yn-2-yl)palmitamide
• CAS No.: 906528-82-3
• Molecular Formula: C₃₁H₅₀N₂O₂
• Molecular Weight: 482.75
• Mol file: 906528-82-3.mol

Synonyms:N-((2R,3R)-3-hydroxy-5-phenyl-1-(pyrrolidin-1-yl)pent-4-yn-2-yl)palmitamide

Chemical Property of N-((2R,3R)-3-hydroxy-5-phenyl-1-(pyrrolidin-1-yl)pent-4-yn-2-yl)palmitamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-((2R,3R)-3-hydroxy-5-phenyl-1-(pyrrolidin-1-yl)pent-4-yn-2-yl)palmitamide

There total 18 articles about N-((2R,3R)-3-hydroxy-5-phenyl-1-(pyrrolidin-1-yl)pent-4-yn-2-yl)palmitamide 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: 32.0%

N-((2R,3R)-3-hydroxy-1-(pyrrolidin-1-yl)pent-4-yn-2-yl)palmitamide (906528-79-8) + iodobenzene (591-50-4) → N-((2R,3R)-3-hydroxy-5-phenyl-1-(pyrrolidin-1-yl)pent-4-yn-2-yl)palmitamide (906528-82-3)

Guidance literature:

With piperidine; bis-triphenylphosphine-palladium(II) chloride; at 70 ℃;

DOI:10.1016/j.bmc.2006.03.048

Reference yield:

(4R)-4-((1R)-1-hydroxy-3-trimethylsilanyl-prop-2-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (129786-70-5) → N-((2R,3R)-3-hydroxy-5-phenyl-1-(pyrrolidin-1-yl)pent-4-yn-2-yl)palmitamide (906528-82-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

2: 93 percent / acetic acid / 5 h / 60 °C

3: 89 percent / imidazole; 4-dimethylaminopyridine / dimethylformamide / 16 h / 20 °C

4: 98 percent / p-TsOH*H₂O / acetone / 6 h / Heating

5: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.25 h / 20 °C

6: 99 percent / piperidine / PdCl₂(PPh₃)2 / 70 °C

7: 64 percent / pyridine / 35 h / 20 °C

8: 82 percent / dimethylformamide / 72 h / 45 °C

9: HCl / methanol / 12 h / 50 °C

10: 129 mg / 1-hydroxybenzotriazole; pyridine / dimethylformamide / 48 h / 50 °C

With piperidine; pyridine; 1H-imidazole; hydrogenchloride; dmap; tetrabutyl ammonium fluoride; benzotriazol-1-ol; toluene-4-sulfonic acid; acetic acid; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetone; 6: Sonogashira coupling;

DOI:10.1016/j.bmc.2006.03.048

Reference yield:

(4R)-4-((1R)-1-hydroxy-prop-2-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (160592-94-9) → N-((2R,3R)-3-hydroxy-5-phenyl-1-(pyrrolidin-1-yl)pent-4-yn-2-yl)palmitamide (906528-82-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 93 percent / acetic acid / 5 h / 60 °C

2: 89 percent / imidazole; 4-dimethylaminopyridine / dimethylformamide / 16 h / 20 °C

3: 98 percent / p-TsOH*H₂O / acetone / 6 h / Heating

4: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.25 h / 20 °C

5: 99 percent / piperidine / PdCl₂(PPh₃)2 / 70 °C

6: 64 percent / pyridine / 35 h / 20 °C

7: 82 percent / dimethylformamide / 72 h / 45 °C

8: HCl / methanol / 12 h / 50 °C

9: 129 mg / 1-hydroxybenzotriazole; pyridine / dimethylformamide / 48 h / 50 °C

With piperidine; pyridine; 1H-imidazole; hydrogenchloride; dmap; tetrabutyl ammonium fluoride; benzotriazol-1-ol; toluene-4-sulfonic acid; acetic acid; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetone; 5: Sonogashira coupling;

DOI:10.1016/j.bmc.2006.03.048

upstream raw materials:

N-((2R,3R)-3-hydroxy-1-(pyrrolidin-1-yl)pent-4-yn-2-yl)palmitamide

iodobenzene

4-nitrophenyl palmitate

(4R,5R)-tert-butyl 5-ethenyl-4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate