472968-69-7

Usage

Uses

Used in Medicinal Chemistry:
2,2,2-Trichloro-acetimidic acid (2R,3R)-3-(4-fluoro-phenyl)-4-((R)-1-phenyl-ethyl)-morpholin-2-yl ester is used as a pharmaceutical intermediate for the development of new drugs. Its unique structure and functional groups, including the trichloro-acetimidic acid moiety and the chiral center, may offer advantages in the design and synthesis of bioactive compounds with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 2,2,2-Trichloro-acetimidic acid (2R,3R)-3-(4-fluoro-phenyl)-4-((R)-1-phenyl-ethyl)-morpholin-2-yl ester serves as a versatile building block for the synthesis of various organic compounds. Its functional groups and structural features can be exploited in a range of chemical reactions, enabling the creation of novel molecules with diverse properties and potential applications.
Used in Chemical Research:
2,2,2-Trichloro-acetimidic acid (2R,3R)-3-(4-fluoro-phenyl)-4-((R)-1-phenyl-ethyl)-morpholin-2-yl ester is utilized as a research tool in chemical investigations. Its complex structure and functional groups provide opportunities for studying reaction mechanisms, exploring the effects of chirality on chemical behavior, and understanding the influence of specific substituents on the properties of organic compounds.

Upstream product

• 545-06-2 trichloroacetonitrile 
• 472968-68-6 (2S,3R)-3-(4-fluorophenyl)-4-[(1R)-1-phenylethyl]-2-morpholinol 
• 80548-31-8 (R)-(+)-N-(2-hydroxyethyl)-α-phenylethylamine 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 447-43-8 1-(4-fluorophenyl)-2,2-dihydroxyethan-1-one 

Downstream Products

• 472968-70-0 (2R,3R)-2-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-3-(4-fluoro-phenyl)-4-((R)-1-phenyl-ethyl)-morpholine 
• 171482-05-6 (2R,3R)-2-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-3-(4-fluoro-phenyl)-morpholine; hydrochloride 
• 171482-05-6 C₂₀H₁₈F₇NO₂*ClH 
• 380499-06-9 (2R,3R)-2-[(1R)-1-(3,5-bis-trifluoro-methylphenyl)ethoxy]-3-(4-fluorophenyl)morpholine 
• 380499-07-0 (2R)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-5,6-dihydro-2H-1,4-oxazine 
• 171338-27-5 [2R-[2α(R*),3α]]-2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine 
• 170729-80-3 aprepitant 

Relevant academic research and scientific papers

Preparation methods of aprepitant impurity

The invention discloses preparation methods of an aprepitant impurity, which comprise isomer impurity synthesis method of six aprepitant key intermediates (2R, 3S)-2-[(1R)-1-[3, 5-bis (trifluoromethyl)-phenyl] ethoxy]-3-(4-fluorophenyl) morpholine, respectively, synthesis of four diastereomer impurities, synthesis of one enantiomer impurity and synthesis of one by-product impurity. The methods have the beneficial effects that the five synthesis methods are simple and feasible, the raw materials are easy to obtain, the conditions are mild, the cost is low, the production is facilitated, and meanwhile, the isomer impurities of the synthesized aprepitant key intermediate provide a new intermediate raw material for the preparation of aprepitant.

Practical asymmetric synthesis of aprepitant, a potent human NK-1 receptor antagonist, via a stereoselective Lewis acid-catalyzed trans acetalization reaction

A streamlined and high-yielding synthesis of aprepitant (1), a potent substance P (SP) receptor antagonist, is described. The enantiopure oxazinone 16 starting material was synthesized via a novel crystallization-induced dynamic resolution process. Conversion of 16 to the penultimate intermediate cis-sec-amine 9 features a highly stereoselective Lewis acid-catalyzed trans acetalization of chiral alcohol 3 with trichloroacetimidate 18 followed by inversion of the adjacent chiral center on the morpholine ring. The six-step process for the synthesis of 9 was accomplished in extremely high overall yield (81%) and with only two isolations.