3-(2-hydroxyethyl)-4-pentenoic acid (1-phenylethyl) amide

Base Information

• Chemical Name: 3-(2-hydroxyethyl)-4-pentenoic acid (1-phenylethyl) amide
• CAS No.: 913617-76-2
• Molecular Formula: C₁₅H₂₁NO₂
• Molecular Weight: 247.337
• Mol file: 913617-76-2.mol

Synonyms:

Chemical Property of 3-(2-hydroxyethyl)-4-pentenoic acid (1-phenylethyl) amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2-hydroxyethyl)-4-pentenoic acid (1-phenylethyl) amide

There total 1 articles about 3-(2-hydroxyethyl)-4-pentenoic acid (1-phenylethyl) amide 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:

(S)-1-phenyl-ethylamine (2627-86-3) + 4-vinyltetrahydro-2H-pyran-2-one (89030-33-1) → 3-(2-hydroxyethyl)-4-pentenoic acid (1-phenylethyl) amide (913617-74-0) + 3-(2-hydroxyethyl)-4-pentenoic acid (1-phenylethyl) amide (913617-76-2)

Guidance literature:

In tetrahydrofuran; at 50 ℃; for 48h;

DOI:10.1016/j.tet.2006.08.068

Reference yield:

3-(2-hydroxyethyl)-4-pentenoic acid (1-phenylethyl) amide (913617-76-2) → benzoic acid 4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-(6-methoxycarbonyl-2-methyl-hex-2-enyl)-cyclopent-2-enyl ester

Guidance literature:

Multi-step reaction with 12 steps

1.1: H₂SO₄ / H₂O; dioxane / Heating

2.1: camphorsulfonic acid / benzene / Heating

3.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

3.2: 94 percent / 3 h

4.1: 98 percent / DIBAL-H / hexane; tetrahydrofuran / -78 - -20 °C

5.1: 94 percent / tetrahydrofuran / 1 h / 0 °C

6.1: 80 percent / second generation Grubbs catalyst / 1.5 h / 20 °C

7.1: 98 percent / triethylamine; 4-dimethylaminopyridine / dimethylformamide / 1 h / 0 °C

8.1: 78 percent / pyridine; 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

9.1: 80 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / 0 °C

10.1: 99 percent / sodium periodate / 2-methyl-propan-2-ol / 2 h / 20 °C

11.1: 76 percent / NaHMDS / tetrahydrofuran / 2 h / 20 °C

12.1: 280 mg / diethyl ether

With pyridine; dmap; sodium periodate; sulfuric acid; sodium hexamethyldisilazane; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; camphor-10-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 11.1: Wittig reaction;

DOI:10.1016/j.tet.2006.08.068

Reference yield:

3-(2-hydroxyethyl)-4-pentenoic acid (1-phenylethyl) amide (913617-76-2) → benzoic acid 4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-(6-carboxy-2-methyl-hex-2-enyl)-cyclopent-2-enyl ester

Guidance literature:

Multi-step reaction with 11 steps

1.1: H₂SO₄ / H₂O; dioxane / Heating

2.1: camphorsulfonic acid / benzene / Heating

3.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

3.2: 94 percent / 3 h

4.1: 98 percent / DIBAL-H / hexane; tetrahydrofuran / -78 - -20 °C

5.1: 94 percent / tetrahydrofuran / 1 h / 0 °C

6.1: 80 percent / second generation Grubbs catalyst / 1.5 h / 20 °C

7.1: 98 percent / triethylamine; 4-dimethylaminopyridine / dimethylformamide / 1 h / 0 °C

8.1: 78 percent / pyridine; 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

9.1: 80 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / 0 °C

10.1: 99 percent / sodium periodate / 2-methyl-propan-2-ol / 2 h / 20 °C

11.1: 76 percent / NaHMDS / tetrahydrofuran / 2 h / 20 °C

With pyridine; dmap; sodium periodate; sulfuric acid; sodium hexamethyldisilazane; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; camphor-10-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 11.1: Wittig reaction;

DOI:10.1016/j.tet.2006.08.068

upstream raw materials:

(S)-1-phenyl-ethylamine

4-vinyltetrahydro-2H-pyran-2-one

Downstream raw materials:

benzoic acid 5-(6-methoxy-carbonyl-2-hexenyl-4-2-octenyl)-2-cyclopentenyl ester

benzoic acid 4-[2(tert-butyldiphenylsilanyloxy)ethyl]-5-(2-oxoethyl)-2-cyclopentenyl ester

Benzoic acid (4R,5R)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-(3,3-dimethyl-oxiranylmethyl)-cyclopent-2-enyl ester