2,2,2-Trifluoroethyl trifluoromethanesulfonate → HCID 90042077, compound

Temperature

80 °C

Diisopropylethylamine (0.26 ml, 1.489 mmol) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.13 ml, 0.902 mmol) were added to a stirred solution of 3-(4-bromophenyl)pyrrolidine 2,2,2-trifluoroacetate (254.5 mg, 0.748 mmol) in dioxane (3.0 ml). The reaction mixture was heated to 80° C. After 17 hours, the reaction mixture was cooled to room temperature and evaporated under reduced pressure to give a yellow residue. The residue was dissolved in dichloromethane and loaded onto a 5 g silica solid load cartridge. The residue was purified using an ISCO Rf and a 12 g silica column (CV=16.8 ml). The column was eluted as follows: 100% dichloromethane (3 CV), 0-3% MeOH/dichloromethane gradient (17 CV), 3% MeOH/dichloromethane (10 CV), 3-5% MeOH/dichloromethane gradient (15 CV), 5% MeOH/dichloromethane (5 CV) at 30 ml/min. The product fractions were combined and evaporated under reduced pressure to give the title compound as a yellow oil. LC-MS: calculated for C12H13BrF3N 307.02, 309.02 observed m/e: 308.05, 310.05 (M+H)+ (Rt 1.02/2 min).

1. temperaturethe reaction mixture was cooled to room temperature
2. customevaporated under reduced pressure
3. customto give a yellow residue
4. customThe residue was purified
5. washThe column was eluted
6. customevaporated under reduced pressure

ORD record

ord-70c65a3773994caaa6ae124a5a5ff5cf

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290517B2