Benzeneacetic acid, α-hydroxy-, (αS)-(2R)-compd. with 2-(4-fluoro-2-methylphenyl)-4-piperidinone (1:1)

Base Information

• Chemical Name: Benzeneacetic acid, α-hydroxy-, (αS)-(2R)-compd. with 2-(4-fluoro-2-methylphenyl)-4-piperidinone (1:1)
• CAS No.: 414910-13-7
• Molecular Formula: C12H14FNO.C8H8O3
• Molecular Weight: 359.39100
• Mol file: 414910-13-7.mol

Synonyms:Benzeneacetic acid, α-hydroxy-, (αS)-, compd. with (2R)-2-(4-fluoro-2-methylphenyl)-4-piperidinone (1:1) (9CI);2-(R)-(4-Fluoro-2-methylphenyl)piperidin-4-one L-(+)-mandelic acid;

Chemical Property of Benzeneacetic acid, α-hydroxy-, (αS)-(2R)-compd. with 2-(4-fluoro-2-methylphenyl)-4-piperidinone (1:1)

Chemical Property:

• Melting Point: 82 - 85 °C
• PSA: 86.63000
• LogP: 3.26110

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzeneacetic acid, α-hydroxy-, (αS)-(2R)-compd. with 2-(4-fluoro-2-methylphenyl)-4-piperidinone (1:1)

There total 4 articles about Benzeneacetic acid, α-hydroxy-, (αS)-(2R)-compd. with 2-(4-fluoro-2-methylphenyl)-4-piperidinone (1:1) 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: 46.0%

2-(4-fluoro-2-methylphenyl)-4-piperidinone camphor-10-sulfonate (579475-69-7) + (S)-Mandelic acid (17199-29-0) → (2R)-2-(4-fluoro-2-methylphenyl)-4-piperidinone L-(+)-mandelate (414910-13-7)

Guidance literature:

2-(4-fluoro-2-methylphenyl)-4-piperidinone camphor-10-sulfonate; With sodium hydrogencarbonate; In dichloromethane; water; for 0.5h; Inert atmosphere; Large scale reaction;

(S)-Mandelic acid; In isopropyl alcohol; at 20 ℃; Inert atmosphere; Large scale reaction;

DOI:10.1021/jm1013264

Reference yield:

4-methoxypyridine (620-08-6,1232006-56-2) → (2R)-2-(4-fluoro-2-methylphenyl)-4-piperidinone L-(+)-mandelate (414910-13-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: iodine; magnesium / tetrahydrofuran / 35 - 70 °C / Inert atmosphere; Reflux; Large scale reaction

1.2: -20 - 30 °C / Inert atmosphere; Large scale reaction

2.1: Wilkinson's catalyst; hydrogen / isopropyl alcohol / 5 h / 50 - 60 °C / 3750.38 Torr / Inert atmosphere; Large scale reaction

3.1: 5% Pd(II)/C(eggshell); hydrogen / isopropyl alcohol / 5 h / 20 °C / 3000.3 Torr / Inert atmosphere; Large scale reaction

3.2: Inert atmosphere; Large scale reaction

4.1: sodium hydrogencarbonate / dichloromethane; water / 0.5 h / Inert atmosphere; Large scale reaction

4.2: 20 °C / Inert atmosphere; Large scale reaction

With Wilkinson's catalyst; 5% Pd(II)/C(eggshell); hydrogen; iodine; sodium hydrogencarbonate; magnesium; In tetrahydrofuran; dichloromethane; water; isopropyl alcohol; 1.2: Comins type reaction;

DOI:10.1021/jm1013264

Reference yield:

2-Bromo-5-fluorotoluene (452-63-1) → (2R)-2-(4-fluoro-2-methylphenyl)-4-piperidinone L-(+)-mandelate (414910-13-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: iodine; magnesium / tetrahydrofuran / 35 - 70 °C / Inert atmosphere; Reflux; Large scale reaction

1.2: -20 - 30 °C / Inert atmosphere; Large scale reaction

2.1: Wilkinson's catalyst; hydrogen / isopropyl alcohol / 5 h / 50 - 60 °C / 3750.38 Torr / Inert atmosphere; Large scale reaction

3.1: 5% Pd(II)/C(eggshell); hydrogen / isopropyl alcohol / 5 h / 20 °C / 3000.3 Torr / Inert atmosphere; Large scale reaction

3.2: Inert atmosphere; Large scale reaction

4.1: sodium hydrogencarbonate / dichloromethane; water / 0.5 h / Inert atmosphere; Large scale reaction

4.2: 20 °C / Inert atmosphere; Large scale reaction

With Wilkinson's catalyst; 5% Pd(II)/C(eggshell); hydrogen; iodine; sodium hydrogencarbonate; magnesium; In tetrahydrofuran; dichloromethane; water; isopropyl alcohol; 1.2: Comins type reaction;

DOI:10.1021/jm1013264

upstream raw materials:

4-methoxypyridine

phenylmethyl 2-(4-fluoro-2-methylphenyl)-4-oxo-3,4-dihydro-1(2H)-pyridinecarboxylate

2-(4-fluoro-2-methylphenyl)-4-piperidinone camphor-10-sulfonate

(S)-Mandelic acid

Downstream raw materials:

(2R)-N-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-2-(4-fluoro-2-methylphenyl)-N-methyl-4-oxo-1-piperidinecarboxamide

C₂₅H₂₈F₇N₃O

C₂₅H₂₈F₇N₃O

C₂₆H₃₀F₇N₃O