Trifluoro-acetic acid (2S,4R)-2-phenyl-1-(2,2,2-trifluoro-acetyl)-piperidin-4-yl ester

Base Information

• Chemical Name: Trifluoro-acetic acid (2S,4R)-2-phenyl-1-(2,2,2-trifluoro-acetyl)-piperidin-4-yl ester
• CAS No.: 1026470-49-4
• Molecular Formula: C₁₅H₁₃F₆NO₃
• Molecular Weight: 369.264
• Mol file: 1026470-49-4.mol

Synonyms:

Chemical Property of Trifluoro-acetic acid (2S,4R)-2-phenyl-1-(2,2,2-trifluoro-acetyl)-piperidin-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Trifluoro-acetic acid (2S,4R)-2-phenyl-1-(2,2,2-trifluoro-acetyl)-piperidin-4-yl ester

There total 11 articles about Trifluoro-acetic acid (2S,4R)-2-phenyl-1-(2,2,2-trifluoro-acetyl)-piperidin-4-yl 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:

trifluoroacetic anhydride (407-25-0) + (2S,4R)-(-)-2-Phenylpiperidine-4-ol (259856-83-2) → Trifluoro-acetic acid (2S,4R)-2-phenyl-1-(2,2,2-trifluoro-acetyl)-piperidin-4-yl ester (1026470-49-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 23 ℃; for 12h;

DOI:10.1016/S0957-4166(99)00458-9

Reference yield:

2-Phenyl-[1,3]dithiane (5425-44-5) → Trifluoro-acetic acid (2S,4R)-2-phenyl-1-(2,2,2-trifluoro-acetyl)-piperidin-4-yl ester (1026470-49-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 2 h / -25 °C

1.2: 83 percent / tetrahydrofuran / 5 h

2.1: aq.nBu₄NF / tetrahydrofuran / 1 h / 0 °C

3.1: K₂CO₃ / tetrahydrofuran / 12 h / 20 °C

4.1: 80 percent / LiClO₄ / acetonitrile / 70 °C

5.1: 80 percent / Hg(ClO₄)2; CaCO₃ / tetrahydrofuran; H₂O / 2 h / 20 °C

6.1: 33 percent / H₂ / PtO₂ / ethanol / 12 h / 20 °C

7.1: Et₃N; dimethylaminopyridine / CH₂Cl₂ / 12 h / 23 °C

With dmap; n-butyllithium; mercury(II) perchlorate; tetrabutyl ammonium fluoride; hydrogen; lithium perchlorate; potassium carbonate; triethylamine; calcium carbonate; platinum(IV) oxide; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; acetonitrile; 1.1: Metallation / 1.2: Condensation / 2.1: selective deprotection / 3.1: Cyclization / 4.1: Alkylation / 5.1: Hydrolysis / 6.1: Hydrogenation / 7.1: Acetylation;

DOI:10.1016/S0957-4166(99)00458-9

Reference yield:

(2S)-4-(1,3-dithian-2-yl)-1,2-epoxy-4-phenylbutane (259856-85-4) → Trifluoro-acetic acid (2S,4R)-2-phenyl-1-(2,2,2-trifluoro-acetyl)-piperidin-4-yl ester (1026470-49-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / LiClO₄ / acetonitrile / 70 °C

2: 80 percent / Hg(ClO₄)2; CaCO₃ / tetrahydrofuran; H₂O / 2 h / 20 °C

3: 33 percent / H₂ / PtO₂ / ethanol / 12 h / 20 °C

4: Et₃N; dimethylaminopyridine / CH₂Cl₂ / 12 h / 23 °C

With dmap; mercury(II) perchlorate; hydrogen; lithium perchlorate; triethylamine; calcium carbonate; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile; 1: Alkylation / 2: Hydrolysis / 3: Hydrogenation / 4: Acetylation;

DOI:10.1016/S0957-4166(99)00458-9

upstream raw materials:

trifluoroacetic anhydride

(2S,4R)-(-)-2-Phenylpiperidine-4-ol

(R,E)-N-benzylidene-4-methylbenzenesulfinamide

6-phenyl-5,6-dihydro-2,4(1H,3H)-pyridinedione

Downstream raw materials:

(2S,4R)-4-hydroxypiperidine-2-carboxylic acid

(2S,4R)-(-)-4-Acetoxy-2-phenyl-1-trifluoroacetylpiperidine