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

Base Information

• Chemical Name: 2,2,2-Trichloro-acetimidic acid (2R,3R)-3-(4-fluoro-phenyl)-4-((R)-1-phenyl-ethyl)-morpholin-2-yl ester
• CAS No.: 472968-69-7
• Molecular Formula: C₂₀H₂₀Cl₃FN₂O₂
• Molecular Weight: 445.748
• Mol file: 472968-69-7.mol

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

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

Chemical Property:

• Boiling Point: 450.6±55.0 °C(Predicted)
• Density: 1.37±0.1 g/cm3(Predicted)

Purity/Quality:

98% HPLC ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about 2,2,2-Trichloro-acetimidic acid (2R,3R)-3-(4-fluoro-phenyl)-4-((R)-1-phenyl-ethyl)-morpholin-2-yl ester 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:

trichloroacetonitrile (545-06-2) + (2S,3R)-3-(4-fluorophenyl)-4-[(1R)-1-phenylethyl]-2-morpholinol (472968-68-6) → 2,2,2-Trichloro-acetimidic acid (2R,3R)-3-(4-fluoro-phenyl)-4-((R)-1-phenyl-ethyl)-morpholin-2-yl ester (472968-69-7)

Guidance literature:

With potassium carbonate; In toluene; at 20 ℃; for 5h;

DOI:10.1021/jo0203793

Reference yield:

(3R)-[3-(4-fluorophenyl)]-4-[(1R)-1-phenylethyl]-2-morpholinone → 2,2,2-Trichloro-acetimidic acid (2R,3R)-3-(4-fluoro-phenyl)-4-((R)-1-phenyl-ethyl)-morpholin-2-yl ester (472968-69-7)

Guidance literature:

Multi-step reaction with 2 steps

1: DIBALH / toluene; tetrahydrofuran / 0.5 h / -20 °C

2: K₂CO₃ / toluene / 5 h / 20 °C

With diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; toluene;

DOI:10.1021/jo0203793

Reference yield:

C17H19NO2 → 2,2,2-Trichloro-acetimidic acid (2R,3R)-3-(4-fluoro-phenyl)-4-((R)-1-phenyl-ethyl)-morpholin-2-yl ester (472968-69-7)

Guidance literature:

Multi-step reaction with 6 steps

1: hydrogenchloride / ethyl acetate; water / 1 h / 20 °C

2: sodium hydroxide; water / methanol / 2 h / 20 - 25 °C

3: acetic acid / Isopropyl acetate / 3 h / Reflux; Inert atmosphere

4: hydrogenchloride / 70 - 75 °C

5: sodium hydrogencarbonate / water; toluene / 20 °C

6: potassium carbonate / toluene / 5 h / 20 - 25 °C / Inert atmosphere

With hydrogenchloride; water; sodium hydrogencarbonate; potassium carbonate; acetic acid; sodium hydroxide; In methanol; Isopropyl acetate; water; ethyl acetate; toluene;

upstream raw materials:

trichloroacetonitrile

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

(R)-(+)-N-(2-hydroxyethyl)-α-phenylethylamine

1-(4-fluorophenyl)ethanone

Downstream raw materials:

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

C₂₀H₁₈F₇NO₂*ClH

(2R,3R)-2-[(1R)-1-(3,5-bis-trifluoro-methylphenyl)ethoxy]-3-(4-fluorophenyl)morpholine

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

Refernces

• 1、 Zhao, Matthew M.,McNamara, James M.,Ho, Guo-Jie,Emerson, Khateeta M.,Song, Zhiguo J.,Tschaen, David M.,Brands, Karel M. J.,Dolling, Ulf-H,Grabowski, Edward J. J.,Reider, Paul J.,Cottrell, Ian F.,Ashwood, Michael S.,Bishop, Brian C.. "Practical asymmetric synthesis of aprepitant, a potent human NK-1 receptor antagonist, via a stereoselective Lewis acid-catalyzed trans acetalization reaction". . p. 6743 - 6747. Retrieved 2007/10/03.