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

Base Information

• Chemical Name: (2R,3S)-2-((R)-1-(3,5-Bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholine hydrochloride
• CAS No.: 171482-05-6
• Molecular Formula: C₂₀H₁₈F₇NO₂*ClH
• Molecular Weight: 473.818
• European Community (EC) Number: 691-262-0
• DSSTox Substance ID: DTXSID10435824
• Mol file: 171482-05-6.mol

Synonyms:171482-05-6;(2R,3S)-2-((R)-1-(3,5-Bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholine hydrochloride;(2R,3S)-2-[(1R)-1-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]ETHOXY]-3-(4-FLUOROPHENYL)MORPHOLINE HYDROCHLORIDE;(2R,3S)-2-{(1R)-1-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]ETHOXY}-3-(4-FLUOROPHENYL)MORPHOLINE HYDROCHLORIDE;(2R,3S)-2-((R)-1-(3,5-Bis(trifluoromethyl)phenyl)-ethoxy)-3-(4-fluorophenyl)morpholine hydrochloride;(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine;hydrochloride;C20H19ClF7NO2;SCHEMBL14890138;DTXSID10435824;AKOS015995122;AKOS015999565;AM84603;s10990;AC-25506;DS-17845;CS-0158204;A850791;J-500977;(2R,3S)-2-((R)-1-(3,5-Bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholine HCl;(2R,3S)-2-((R)-1-(3,5-Bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholinehydrochloride;(2R,3S)-2-{(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy}-3-(4-fluorophenyl)morpholine--hydrogen chloride (1/1);Morpholine,2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-,hydrochloride, (2R,3S)-

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

Chemical Property:

• Boiling Point: 387.9 °C at 760 mmHg
• Flash Point: 188.4 °C
• PSA: 30.49000
• LogP: 6.75890
• Storage Temp.: Inert atmosphere,Room Temperature
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 473.0992537
• Heavy Atom Count: 31
• Complexity: 526

Purity/Quality:

99.9% ^*data from raw suppliers

(2R,3S)-2-((R)-1-(3,5-Bis(trifluoromethyl)phenyl)-ethoxy)-3-(4-fluorophenyl)morpholine hydrochloride 95+% ^*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.Cl
• 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.Cl

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

There total 43 articles about (2R,3S)-2-((R)-1-(3,5-Bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholine hydrochloride 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: 94.7%

4-flourophenylmagnesium bromide (352-13-6) + (2R,2αR)-4-benzyl-2-[1-[3,5-bis(trifluoromethyl)phenyl]]ethoxy-morpholin-3-one (287930-75-0) → [2R-[2α(R*),3α]]-2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine hydrochloride (171482-05-6)

Guidance literature:

4-flourophenylmagnesium bromide; (2R,2αR)-4-benzyl-2-[1-[3,5-bis(trifluoromethyl)phenyl]]ethoxy-morpholin-3-one; In tetrahydrofuran; methanol; at 15 - 20 ℃; for 0.916667h;

With palladium 10% on activated carbon; ammonium formate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol;

With hydrogenchloride; In di-isopropyl ether; water; for 0.5h; Reflux;

Reference yield: 94.0%

(2R,3R)-2-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-3-(4-fluoro-phenyl)-4-((R)-1-phenyl-ethyl)-morpholine (472968-70-0) → (2R,3R)-2-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-3-(4-fluoro-phenyl)-morpholine; hydrochloride (171482-05-6)

Guidance literature:

With hydrogenchloride; hydrogen; 5percent Pd/C; In methanol;

DOI:10.1021/jo0203793

Reference yield: 93.1%

1-Bromo-4-fluorobenzene (460-00-4) + (2R,2αR)-4-benzyl-2-[1-[3,5-bis(trifluoromethyl)phenyl]]ethoxy-morpholin-3-one (287930-75-0) → [2R-[2α(R*),3α]]-2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine hydrochloride (171482-05-6)

Guidance literature:

1-Bromo-4-fluorobenzene; (2R,2αR)-4-benzyl-2-[1-[3,5-bis(trifluoromethyl)phenyl]]ethoxy-morpholin-3-one; With palladium on activated charcoal; hydrogen; magnesium; In tetrahydrofuran;

With hydrogenchloride; In tetrahydrofuran; water; Reagent/catalyst;

upstream raw materials:

(2R,3R)-2-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-3-(4-fluoro-phenyl)-4-((R)-1-phenyl-ethyl)-morpholine

(R)-[3,5-bis(trifluoromethyl)phenyl]ethanol

(2S,3R)-3-(4-fluorophenyl)-4-[(1R)-1-phenylethyl]-2-morpholinol

2,2,2-Trichloro-acetimidic acid (2R,3R)-3-(4-fluoro-phenyl)-4-((R)-1-phenyl-ethyl)-morpholin-2-yl ester

Downstream raw materials:

[3-[[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-2,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl]phosphonic acid bis(phenylmethyl)ester

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

C₂₇H₃₁F₇N₄O₄

Refernces

• 1、 -. "Preparation methods of aprepitant impurity". Paragraph 0105; 0114-0117. . Retrieved 2020/07/13.
• 2、 -. "High-purity aprepitant preparation method". Paragraph 0020-0025. . Retrieved 2020/01/25.