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

Base Information

• Chemical Name: (S)-((R)-1-phenyl-2,2,2-trichloroethyl) 2-(4-chlorophenyl)aziridine-1-carboxylate
• CAS No.: 1374003-35-6
• Molecular Formula: C₁₇H₁₃Cl₄NO₂
• Molecular Weight: 405.108
• Mol file: 1374003-35-6.mol

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

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

There total 6 articles about (S)-((R)-1-phenyl-2,2,2-trichloroethyl) 2-(4-chlorophenyl)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: 70.0%

4-vinylbenzyl chloride (1073-67-2,24991-47-7) + (R)-2,2,2-trichloro-1-phenylethyl N-tosyloxycarbamate → (R)-((R)-1-phenyl-2,2,2-trichloroethyl) 2-(4-chlorophenyl)aziridine-1-carboxylate (1335126-59-4) + (S)-((R)-1-phenyl-2,2,2-trichloroethyl) 2-(4-chlorophenyl)aziridine-1-carboxylate (1374003-35-6)

Guidance literature:

With tetrakis(actonitrile)copper(I) hexafluorophosphate; (4R,4'R)-2,2'-(propane-2,2-diyl)bis(5,5-dimethyl-4-phenyl-4,5-dihydrooxazole); potassium carbonate; In acetonitrile; at 23 ℃; for 14h; optical yield given as %de; diastereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.tet.2012.02.044

Reference yield:

4-vinylbenzyl chloride (1073-67-2,24991-47-7) + (R)-1-phenyl-2,2,2-trichloroethyl N-tosyloxycarbamate (1335126-79-8) → (R)-((R)-1-phenyl-2,2,2-trichloroethyl) 2-(4-chlorophenyl)aziridine-1-carboxylate (1335126-59-4) + (S)-((R)-1-phenyl-2,2,2-trichloroethyl) 2-(4-chlorophenyl)aziridine-1-carboxylate (1374003-35-6)

Guidance literature:

4-vinylbenzyl chloride; (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; diastereoselective reaction;

DOI:10.1021/ol2021516

Reference yield:

(R)-2,2,2-trichloro-1-phenylethyl hydroxycarbamate (1391854-32-2) → (R)-((R)-1-phenyl-2,2,2-trichloroethyl) 2-(4-chlorophenyl)aziridine-1-carboxylate (1335126-59-4) + (S)-((R)-1-phenyl-2,2,2-trichloroethyl) 2-(4-chlorophenyl)aziridine-1-carboxylate (1374003-35-6)

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-vinylbenzyl chloride

(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-(4-chlorophenyl)-2-hydroxyethylcarbamate

(R)-2,2,2-trichloro-1-phenylethyl (S)-2-(4-chlorophenyl)-2-hydroxyethylcarbamate