(S)-((R)-1-phenyl-2,2,2-trichloroethyl) 2-(4-nitrophenyl)aziridine-1-carboxylate

Base Information

• Chemical Name: (S)-((R)-1-phenyl-2,2,2-trichloroethyl) 2-(4-nitrophenyl)aziridine-1-carboxylate
• CAS No.: 1374003-18-5
• Molecular Formula: C₁₇H₁₃Cl₃N₂O₄
• Molecular Weight: 415.66
• Mol file: 1374003-18-5.mol

Synonyms:(S)-((R)-1-phenyl-2,2,2-trichloroethyl) 2-(4-nitrophenyl)aziridine-1-carboxylate

Chemical Property of (S)-((R)-1-phenyl-2,2,2-trichloroethyl) 2-(4-nitrophenyl)aziridine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-((R)-1-phenyl-2,2,2-trichloroethyl) 2-(4-nitrophenyl)aziridine-1-carboxylate

There total 5 articles about (S)-((R)-1-phenyl-2,2,2-trichloroethyl) 2-(4-nitrophenyl)aziridine-1-carboxylate 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: 63.0%

4-nitrostyrene (100-13-0) + (R)-1-phenyl-2,2,2-trichloroethyl N-tosyloxycarbamate (1335126-79-8) → (S)-((R)-1-phenyl-2,2,2-trichloroethyl) 2-(4-nitrophenyl)aziridine-1-carboxylate (1374003-18-5) + (R)-((R)-1-phenyl-2,2,2-trichloroethyl) 2-(4-nitrophenyl)aziridine-1-carboxylate (1335126-58-3)

Guidance literature:

4-nitrostyrene; (R)-1-phenyl-2,2,2-trichloroethyl N-tosyloxycarbamate; With [Rh₂{(S)-4-Br-nttl}4]; In 4-methyl-1,2,3-trifluorobenzene; for 0.0833333h;

With potassium carbonate; In 4-methyl-1,2,3-trifluorobenzene; at 23 ℃; for 1.5h; optical yield given as %de;

DOI:10.1021/ol2021516

Reference yield:

C12H9Cl3N2O2 → (S)-((R)-1-phenyl-2,2,2-trichloroethyl) 2-(4-nitrophenyl)aziridine-1-carboxylate (1374003-18-5) + (R)-((R)-1-phenyl-2,2,2-trichloroethyl) 2-(4-nitrophenyl)aziridine-1-carboxylate (1335126-58-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1H-imidazole; hydroxylamine hydrochloride / acetonitrile / 1 h / 0 °C

2.1: triethylamine / diethyl ether / 1 h / 0 °C

3.1: [Rh₂{(S)-4-Br-nttl}4] / 4-methyl-1,2,3-trifluorobenzene / 0.08 h

3.2: 1.5 h / 23 °C

With 1H-imidazole; [Rh₂{(S)-4-Br-nttl}4]; hydroxylamine hydrochloride; triethylamine; In diethyl ether; acetonitrile; 4-methyl-1,2,3-trifluorobenzene;

DOI:10.1021/ol2021516

Reference yield:

(R)-2,2,2-trichloro-1-phenylethyl hydroxycarbamate (1391854-32-2) → (S)-((R)-1-phenyl-2,2,2-trichloroethyl) 2-(4-nitrophenyl)aziridine-1-carboxylate (1374003-18-5) + (R)-((R)-1-phenyl-2,2,2-trichloroethyl) 2-(4-nitrophenyl)aziridine-1-carboxylate (1335126-58-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / diethyl ether / 1 h / 0 °C

2.1: [Rh₂{(S)-4-Br-nttl}4] / 4-methyl-1,2,3-trifluorobenzene / 0.08 h

2.2: 1.5 h / 23 °C

With [Rh₂{(S)-4-Br-nttl}4]; triethylamine; In diethyl ether; 4-methyl-1,2,3-trifluorobenzene;

DOI:10.1021/ol2021516

upstream raw materials:

4-nitrostyrene

(R)-1-phenyl-2,2,2-trichloroethyl N-tosyloxycarbamate

(R)-2,2,2-trichloro-1-phenylethyl hydroxycarbamate

2,2,2-trichloroacetophenone

Downstream raw materials:

(R)-2,2,2-trichloro-1-phenylethyl (R)-2-methoxy-2-(4-nitrophenyl)ethylcarbamate

(-)-Nifenalol

(R)-1-(4-nitrophenyl)-2-(((R)-2,2,2-trichloro-1-phenylethoxy)carbonylamino)ethyl acetate

(S)-1-(4-nitrophenyl)-2-(((R)-2,2,2-trichloro-1-phenylethoxy)carbonylamino)ethyl acetate