380499-07-0

Basic information

• Product Name: (2R)-2-[(1R)-1-[3,5-Bis(trifluoroMethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-5,6-dihydro-2H-1,4-oxazine
• Synonyms: (2R)-2-[(1R)-1-[3,5-Bis(trifluoroMethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-5,6-dihydro-2H-1,4-oxazine;Aprepitant dehydro dealkyl
• CAS NO: 380499-07-0
• Molecular Formula: C₂₀H₁₆F₇NO₂
• Molecular Weight: 435
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 380499-07-0.mol

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Ethyl Acetate
• CAS DataBase Reference: (2R)-2-[(1R)-1-[3,5-Bis(trifluoroMethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-5,6-dihydro-2H-1,4-oxazine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2-[(1R)-1-[3,5-Bis(trifluoroMethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-5,6-dihydro-2H-1,4-oxazine(380499-07-0)
• EPA Substance Registry System: (2R)-2-[(1R)-1-[3,5-Bis(trifluoroMethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-5,6-dihydro-2H-1,4-oxazine(380499-07-0)

Safety Data

• Hazardous Substances Data: 380499-07-0(Hazardous Substances Data)

Usage

Uses

1. Pharmaceutical Industry:
(2R)-2-[(1R)-1-[3,5-Bis(trifluoroMethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-5,6-dihydro-2H-1,4-oxazine is used as an intermediate in the preparation of enantiomerically pure Aprepitant diastereomers and derivatives. (2R)-2-[(1R)-1-[3,5-Bis(trifluoroMethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-5,6-dihydro-2H-1,4-oxazine's stereochemistry plays a vital role in the development of these pharmaceuticals, ensuring the desired biological activity and minimizing potential side effects.
2. Chemical Synthesis:
As an intermediate, (2R)-2-[(1R)-1-[3,5-Bis(trifluoroMethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-5,6-dihydro-2H-1,4-oxazine can be utilized in various chemical synthesis processes. Its unique structure and functional groups make it a valuable building block for creating novel compounds with specific applications in different industries.
3. Research and Development:
(2R)-2-[(1R)-1-[3,5-Bis(trifluoroMethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-5,6-dihydro-2H-1,4-oxazine's specific stereochemistry and chemical properties make it an interesting subject for research and development. Scientists and researchers can explore its potential applications in various fields, such as materials science, pharmaceuticals, and agrochemicals, by studying its interactions with other molecules and its reactivity under different conditions.

Upstream product

• 1765-93-1 4-fluoroboronic acid 
• 1185503-03-0 4-benzyl-3-(4-fluorophenyl)morpholin-2-ol 
• 1185503-15-4 (+/-)-trans-4-benzyl-2-[2-(3,5-bis-trifluoromethylphenyl)ethoxy]-3-(4-fluorophenyl)morphine 
• 1185503-10-9 (2S,3R)-4-benzyl-3-(4-fluorophenyl)morpholin-2-ol 
• 472968-70-0 (2R,3R)-2-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-3-(4-fluoro-phenyl)-4-((R)-1-phenyl-ethyl)-morpholine 
• 380499-06-9 (2R,3R)-2-[(1R)-1-(3,5-bis-trifluoro-methylphenyl)ethoxy]-3-(4-fluorophenyl)morpholine 
• 472968-69-7 2,2,2-Trichloro-acetimidic acid (2R,3R)-3-(4-fluoro-phenyl)-4-((R)-1-phenyl-ethyl)-morpholin-2-yl ester 
• 472968-68-6 (2S,3R)-3-(4-fluorophenyl)-4-[(1R)-1-phenylethyl]-2-morpholinol 
• 368-63-8 (R)-[3,5-bis(trifluoromethyl)phenyl]ethanol 

Downstream Products

• 171338-27-5 [2R-[2α(R*),3α]]-2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine 
• 380499-06-9 (2R,3R)-2-[(1R)-1-(3,5-bis-trifluoro-methylphenyl)ethoxy]-3-(4-fluorophenyl)morpholine 
• 170729-80-3 aprepitant 

Relevant articles and documents

Synthesis of all enantiomerically pure diastereomers of aprepitant

Syntheses of all eight enantiomerically pure diastereomers of aprepitant and assignment of absolute configuration at newly generated stereocenters by NMR and X-ray crystallographic analysis were achieved. Copyrigh

PREPARATION OF MORPHOLINE DERIVATIVES

This invention relates to processes and intermediates for the stereoselective morpholine derivatives. The invention in particular allows the stereoselective preparation of the drugs aprepitant and fosaprepitant.

PREPARATION OF APREPITANT

A process for preparing aprepitant.

A convergent approach to the synthesis of aprepitant: a potent human NK-1 receptor antagonist

A simple and convergent approach to enantiomerically pure 5-[[2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy-3-(4-fluorophenyl)morpholin-4-yl]methyl]-1,2-dihydro-1,2,4-triazol-3-one 1, a potent orally active antagonist of the human neurokinin-1 (NK-1) receptor, is described. The synthetic procedure starts from p-fluorobenzaldehyde to access the racemic morpholinone 2 via a modified Strecker synthesis and utilizes a diastereomeric salt resolution technique to accomplish the synthesis of 1 in enantiomerically pure form and good yield.

Mammalian metabolites of a tachykinin receptor antagonist

This invention is concerned with mammalian metabolites of the compound 2-(R)-(1-(R)-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-3-(S)-(4-fluoro)-phenyl-4-(3-(5-oxo-1H,4H-1,2,4-triazolo)methylmorpholine which is a tachykinin receptor antagonist that is useful

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.