(2R,3S)-2-((R)-1-(3,5-Bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholine

Base Information

• Chemical Name: (2R,3S)-2-((R)-1-(3,5-Bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholine
• CAS No.: 171338-27-5
• Molecular Formula: C20H18F7NO2
• Molecular Weight: 437.357
• UNII: EA5SX368WV
• DSSTox Substance ID: DTXSID00435818
• Nikkaji Number: J1.409.246C
• Wikidata: Q27277068
• Mol file: 171338-27-5.mol

Synonyms:171338-27-5;(2R,3S)-2-((R)-1-(3,5-Bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholine;2-(R)-[1-(R)-(3,5-Bis(trifluoromethyl)phenyl)ethoxy]-3-(S)-fluorophenylmorpholine[Aprepitant-M2];(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine;UNII-EA5SX368WV;EA5SX368WV;2-((1R)-1-(3,5-Bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl) morpholine, (2R,3S)-;Morpholine, 2-((1R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)-, (2R,3S)-;(2R,3S)-2-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-3-(4-fluorophenyl)morpholine;[Aprepitant-M2];(2R,3S)-2-((R)-1-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-ETHOXY)-3-(4-FLUOROPHENYL)MORPHOLINE;170729-79-0;SCHEMBL264332;DTXSID00435818;BCPP000158;AKOS015908996;BCP9000960;AC-23962;A811318;J-010710;Q27277068;(2R,3S)-2-((1R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl) morpholine;(2S,3R)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine;2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-(2R,3S)-morpholine;2alpha-[(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3alpha-(4-fluorophenyl)morpholine

Chemical Property of (2R,3S)-2-((R)-1-(3,5-Bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.505
• Boiling Point: 387.856 °C at 760 mmHg
• PKA: 6.93±0.60(Predicted)
• Flash Point: 188.369 °C
• PSA: 30.49000
• Density: 1.375 g/cm³
• LogP: 5.99300
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 437.12257595
• Heavy Atom Count: 30
• Complexity: 526

Purity/Quality:

99% ^*data from raw suppliers

2-(R)-[1-(R)-(3,5-Bis(trifluoromethyl)phenyl)ethoxy]-3-(S)-fluorophenylmorpholine[Aprepitant-M2] ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)OC2C(NCCO2)C3=CC=C(C=C3)F
• Isomeric SMILES: C[C@H](C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)O[C@@H]2[C@@H](NCCO2)C3=CC=C(C=C3)F

Technology Process of (2R,3S)-2-((R)-1-(3,5-Bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholine

There total 29 articles about (2R,3S)-2-((R)-1-(3,5-Bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholine 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: 92.2%

C20H18F7NO2 → [2R-[2α(R*),3α]]-2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine (171338-27-5)

Guidance literature:

With diethyl (2S,3S)-tartrate; N-ethyl-N,N-diisopropylamine; calcium chloride; In tert-butyl methyl ether; acetone; at 20 ℃; for 4h; Reagent/catalyst;

Reference yield: 86.0%

(2R)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-5,6-dihydro-2H-1,4-oxazine (380499-07-0) → [2R-[2α(R*),3α]]-2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine (171338-27-5)

Guidance literature:

With potassium formate; palladium on carbon; In ethanol; water; at 20 ℃; for 2h; Product distribution / selectivity;

Reference yield:

2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-5,6-dihydro-2H-1,4-oxazine (1025023-03-3) → [2R-[2α(R*),3α]]-2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine (171338-27-5)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In methanol; at 25 - 30 ℃; for 6.5h; under 112.511 Torr;

upstream raw materials:

(2R)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-5,6-dihydro-2H-1,4-oxazine

4-flourophenylmagnesium bromide

(2R,2αR)-4-benzyl-2-[1-[3,5-bis(trifluoromethyl)phenyl]]ethoxy-morpholin-3-one

C₂₀H₁₆F₇NO₂

Downstream raw materials:

2-[2-[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]-1-iminoethyl]hydrazinecarboxylic acid methyl ester

5-[[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-1,2-dihydro-3H-1,2,4-triazol-3-one

[2R-[2α(R*),3α]]-2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine hydrochloride

aprepitant

Refernces

• 1、 -. "Preparation method of NK1 receptor antagonist". Paragraph 0029-0030; 0032-0033; 0035-0036; 0038-0039; .... . Retrieved 2021/11/03.
• 2、 -. "Reduction of organic compounds with low amounts of hydrogen". Page/Page column 9. . Retrieved 2011/06/23.