(3R)-3-(4-Fluorophenyl)-4-(phenylmethyl)-2-morpholinone

Base Information

• Chemical Name: (3R)-3-(4-Fluorophenyl)-4-(phenylmethyl)-2-morpholinone
• CAS No.: 219821-32-6
• Molecular Formula: C₁₇H₁₆FNO₂
• Molecular Weight: 285.318
• DSSTox Substance ID: DTXSID101205577
• Nikkaji Number: J807.479H
• Mol file: 219821-32-6.mol

Synonyms:SCHEMBL5226630;DTXSID101205577;AKOS015912233;219821-32-6;(3R)-3-(4-Fluorophenyl)-4-(phenylmethyl)-2-morpholinone

Chemical Property of (3R)-3-(4-Fluorophenyl)-4-(phenylmethyl)-2-morpholinone

Chemical Property:

• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 285.11650692
• Heavy Atom Count: 21
• Complexity: 349

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1COC(=O)C(N1CC2=CC=CC=C2)C3=CC=C(C=C3)F
• Isomeric SMILES: C1COC(=O)[C@H](N1CC2=CC=CC=C2)C3=CC=C(C=C3)F

Technology Process of (3R)-3-(4-Fluorophenyl)-4-(phenylmethyl)-2-morpholinone

There total 5 articles about (3R)-3-(4-Fluorophenyl)-4-(phenylmethyl)-2-morpholinone 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:

ethyl 2-(2-(tert-butyldiphenylsilyloxy)ethylamino)-2-(4-fluorophenyl)acetate + benzyl bromide (100-39-0) → 4-benzyl-3-(4-fluorophenyl)morpholin-2-one (159706-87-3) + N-benzyl-3-(R)-(p-fluorophenyl)morpholin-2-one (219821-32-6)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium carbonate; In N,N-dimethyl-formamide; at 100 ℃; for 72h; Overall yield = 91 %; Overall yield = 54 mg; Inert atmosphere;

DOI:10.1021/acs.orglett.7b02627

Reference yield:

(R)-[Benzyl-(2-hydroxy-ethyl)-amino]-(4-fluoro-phenyl)-acetic acid (S)-1-methyl-2-oxo-2-pyrrolidin-1-yl-ethyl ester → 4-benzyl-3-(4-fluorophenyl)morpholin-2-one (159706-87-3) + N-benzyl-3-(R)-(p-fluorophenyl)morpholin-2-one (219821-32-6)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 80 ℃; for 0.5h;

DOI:10.3987/com-02-s(m)54

Reference yield:

(2-methoxy-2-oxo-(S)-1-phenylethyl) α-bromo(p-fluorophenyl)acetate (1224387-68-1) + N-Benzylethanolamine (104-63-2) → 4-benzyl-3-(4-fluorophenyl)morpholin-2-one (159706-87-3) + N-benzyl-3-(R)-(p-fluorophenyl)morpholin-2-one (219821-32-6)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; optical yield given as %ee;

DOI:10.3998/ark.5550190.0011.201

upstream raw materials:

N-Benzylethanolamine

(2-methoxy-2-oxo-(S)-1-phenylethyl) α-bromo(p-fluorophenyl)acetate

benzyl bromide

Downstream raw materials:

(2R,3S)-4-benzyl-2-({1-[3,5-bis(trifluoromethyl)phenyl]-vinyl}oxy)-3-(4-fluorophenyl)morpholine