1,1,1-Trifluoro-N-phenylmethanesulfonamide → 5,5-Dimethyl-1-cyclopenten-1-yl 1,1,1-trifluoromethanesulfonate

Temperature

-78 °C

To a solution of 2,2-dimethylcyclopentanone T6.1 (available from ChemSampCo) (3.00 g, 26.75 mmol) in THF (100 mL), was slowly added LDA (14.7 mL, 2.0 M, in heptane) at −78° C. The resulting mixture was stirred at −78° C. for 1 hour. A solution of N-phenyltriflamide (10.00 g, 28.00 mmol) was added to the mixture at −78° C., and stirring was continued at 0° C. for 2 hours and then at room temperature overnight. The reaction mixture was extracted with hexane (80×2 mL). The organic layer was washed with saturated Na2CO3 (30 mL), brine (20 mL), and dried with MgSO4. The solvent was removed, and the residue was purified by CombiFlash® chromatography (eluant was EtOAc and hexane) to give T6.2. 1H NMR (CDCl3) δ ppm 1.16 (s, 6H), 1.86 (t, J=7.1 Hz, 2H), 2.36 (t, J=7.1 Hz, 2H), 5.56 (m, 1H).

1. customat −78° C
2. stirringstirring
3. waitwas continued at 0° C. for 2 hours
4. customat room temperature
5. customovernight
6. extractionThe reaction mixture was extracted with hexane (80×2 mL)
7. washThe organic layer was washed with saturated Na2CO3 (30 mL), brine (20 mL)
8. dry with materialdried with MgSO4
9. customThe solvent was removed
10. customthe residue was purified by CombiFlash® chromatography (eluant was EtOAc and hexane)
11. customto give T6.2

ORD record

ord-5ebb9a98fc154e5bab94eae2de20c051

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450522B2