ChemicalBook CAS DataBase List R-(+)-2-TRIFLUOROMETHYLOXIRANE

R-(+)-2-TRIFLUOROMETHYLOXIRANE synthesis

6synthesis methods

Product Name:R-(+)-2-TRIFLUOROMETHYLOXIRANE
CAS Number:143142-90-9
Molecular formula:C3H3F3O
Molecular Weight:112.05

359-41-1
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$7.00/1g

143142-90-9
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$45.00/10mg

Yield: 76%

Reaction Conditions:

with (1S,2S)-(+)-1,2-cyclohexanediamino-N,N’-bis(3,5-di-t-butylsalicylidene)cobalt (II);acetic acid in water at 0 - 20;

Steps:

1 Preparation 1(2R)-2-(Trifluoromethyl)oxirane
Add acetic acid (0.89 mL, 0.052 eq) to a solution of (1 S,25)-(+)- 1 ,2-cyclohexanediamino-N,N’-bis(3,5-di-t-bu- tylsalicylidene)cobalt (II) (0.90 g, 0.0050 eq) in toluene (16.65 mL). Stir at room temperature for 30 minutes. Remove the solvent in vacuo. Add toluene (20 mL) and concentrate in vacuo. cool to 00 c. and add 2-(trifluorom- ethyl)oxirane (37.00 g, 330 mmol; 80.0% cc, (2R) is the major enantiomer). Stir for five minutes and add water (0.80 mL, 0.15 eq) dropwise. Allow to slowly warm to room temperature and stir overnight. Vacuum distill at room temperature, collecting the title compound in a cooled flask as a light yellow oil (28.10 g, 76%; 99.8% cc). ‘H NMR (CDC13) ö 2.92-2.94 (m, 1H), 2.98-3.01 (m, 1H), 3.41-3.46 (m, 1H).

References:

Eli Lilly and Company;Clayton, Joshua Ryan US9556153, 2017, B1 Location in patent:Page/Page column 7; 8

431-35-6 Synthesis