(S)-3-hydroxy-4-(2,4,5-trifluorophenyl)butanenitrile

Base Information

• Chemical Name: (S)-3-hydroxy-4-(2,4,5-trifluorophenyl)butanenitrile
• CAS No.: 1283096-74-1
• Molecular Formula: C₁₀H₈F₃NO
• Molecular Weight: 215.175
• Mol file: 1283096-74-1.mol

Synonyms:(S)-3-hydroxy-4-(2,4,5-trifluorophenyl)butanenitrile

Chemical Property of (S)-3-hydroxy-4-(2,4,5-trifluorophenyl)butanenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (S)-3-hydroxy-4-(2,4,5-trifluorophenyl)butanenitrile

There total 15 articles about (S)-3-hydroxy-4-(2,4,5-trifluorophenyl)butanenitrile 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: 92.0%

sodium cyanide (773837-37-9) + (2S)-2-(2,4,5-trifluorobenzyl)-oxirane (1283096-72-9) → (S)-3-hydroxy-4-(2,4,5-trifluorophenyl)butanenitrile (1283096-74-1)

Guidance literature:

With ammonium chloride; In methanol; water; at 50 ℃; for 3h;

Reference yield: 66.0%

sodium cyanide (773837-37-9) + C16H15F3O4S → (S)-3-hydroxy-4-(2,4,5-trifluorophenyl)butanenitrile (1283096-74-1)

Guidance literature:

In N,N-dimethyl-formamide; at 75 ℃; for 19h; Inert atmosphere;

DOI:10.1016/j.tet.2012.01.095

Reference yield:

potassium cyanide + (S)-1-chloro-3-(2,4,5-trifluorophenyl)propan-2-ol (1246960-15-5) → (S)-3-hydroxy-4-(2,4,5-trifluorophenyl)butanenitrile (1283096-74-1)

Guidance literature:

With sodium iodide; In water; N,N-dimethyl-formamide; at 95 ℃; for 3h;

upstream raw materials:

1-bromo-2,4,5-trifluorobenzene

sodium cyanide

(2S)-2-(2,4,5-trifluorobenzyl)-oxirane

1-allyl-2,4,5-trifluorobenzene

Downstream raw materials:

(S)-ethyl 3-hydroxy-4-(2,4,5-trifluorophenyl)butanoate

sitagliptin

(R)-3-azido-1-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]-triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one

(2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine phosphate

Refernces

• 1、 Fistikci, Meryem,Gundogdu, Ozlem,Aktas, Derya,Secen, Hasan,Sahin, M. Fethi,Altundas, Ramazan,Kara, Yunus. "Novel and enantioselective syntheses of (R)- and (S)-3-hydroxy-4-(2,4,5- trifluorophenyl)butanoic acid: A synthon for sitagliptin and its derivatives". experimental part. p. 2607 - 2610. Retrieved 2012/05/20.
• 2、 -. "Process for the synthesis of beta-amino acids and derivatives thereof". . . Retrieved 2012/01/06.