(2R)-3,3,3-trifluoro-2-((1R)-2-hydroxy-1-phenyl-ethylamino)-2-methylpropionitrile

Base Information

• Chemical Name: (2R)-3,3,3-trifluoro-2-((1R)-2-hydroxy-1-phenyl-ethylamino)-2-methylpropionitrile
• CAS No.: 911411-54-6
• Molecular Formula: C₁₂H₁₃F₃N₂O
• Molecular Weight: 258.243
• Mol file: 911411-54-6.mol

Synonyms:(2R)-3,3,3-trifluoro-2-((1R)-2-hydroxy-1-phenyl-ethylamino)-2-methylpropionitrile

Chemical Property of (2R)-3,3,3-trifluoro-2-((1R)-2-hydroxy-1-phenyl-ethylamino)-2-methylpropionitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-3,3,3-trifluoro-2-((1R)-2-hydroxy-1-phenyl-ethylamino)-2-methylpropionitrile

There total 10 articles about (2R)-3,3,3-trifluoro-2-((1R)-2-hydroxy-1-phenyl-ethylamino)-2-methylpropionitrile 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: 59.0%

trimethylsilyl cyanide (7677-24-9) + (2R,2S)-2-methyl-4-(R)-phenyl-2-(trifluoromethyl)oxazolidine (911411-78-4) → (2S)-3,3,3-trifluoro-2-((1R)-2-hydroxy-1-phenyl-ethylamino)-2-methylpropionitrile (911411-55-7) + (2R)-3,3,3-trifluoro-2-((1R)-2-hydroxy-1-phenyl-ethylamino)-2-methylpropionitrile (911411-54-6)

Guidance literature:

trimethylsilyl cyanide; (2R,2S)-2-methyl-4-(R)-phenyl-2-(trifluoromethyl)oxazolidine; With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

With water; sodium hydrogencarbonate; In dichloromethane; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.10.086

Reference yield: 54.0%

trimethylsilyl cyanide (7677-24-9) + (2S,4R)-2-methyl-4-phenyl-2-trifluoromethyl-1,3-oxazolidine (1202059-62-8) → (2S)-3,3,3-trifluoro-2-((1R)-2-hydroxy-1-phenyl-ethylamino)-2-methylpropionitrile (911411-55-7) + (2R)-3,3,3-trifluoro-2-((1R)-2-hydroxy-1-phenyl-ethylamino)-2-methylpropionitrile (911411-54-6)

Guidance literature:

trimethylsilyl cyanide; (2S,4R)-2-methyl-4-phenyl-2-trifluoromethyl-1,3-oxazolidine; With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

With water; sodium hydrogencarbonate; In dichloromethane; for 1h; optical yield given as %de;

DOI:10.1002/ejoc.200900768

Reference yield: 49.0%

(-)-(4R)-2-(trifluoromethyl)-2-methyl-4-phenyl-1,3-oxazolidine + trimethylsilyl cyanide (7677-24-9) → (2S)-3,3,3-trifluoro-2-((1R)-2-hydroxy-1-phenyl-ethylamino)-2-methylpropionitrile (911411-55-7) + (2R)-3,3,3-trifluoro-2-((1R)-2-hydroxy-1-phenyl-ethylamino)-2-methylpropionitrile (911411-54-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo0607717

upstream raw materials:

((E)-2,2,2-trifluoro-1-methylethylidene)((1R)-2-hydroxy-1-phenylethyl)amine

trimethylsilyl cyanide

D-2-phenylglycinol

(2S,4R)-2-methyl-4-phenyl-2-trifluoromethyl-1,3-oxazolidine

Downstream raw materials:

methyl (2R)-3,3,3-trifluoro-2-((1R)-2-hydroxy-1-phenyl-ethylamino)-2-methylpropionate

(R)-(+)-3,3,3-trifluoro-2-amino-2-methylpropianoic acid

(2R)-3,3,3-trifluoro-2-((1R)-2-hydroxy-1-phenyl-ethylamino)-2-methyl-propylamine

Refernces

• 1、 -. "PYRIMIDINONE DERIVATIVES AS ANTIMALARIAL AGENTS". . . Retrieved 2014/01/09.
• 2、 Li, Tian-Wen,Shang, Pei-Hua,Cheng, Chang-Mei,Zhao, Yu-Fen. "A convenient one-pot synthesis of (R)-2-amino-3,3,3-trifluoro-2-methyl-N- phenylpropanamide derivatives". supporting information. p. 134 - 137. Retrieved 2013/02/21.