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 B.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 (eluent was EtOAc and hexane) to give B.2. 1H NMR (CDCl3) δ 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 (eluent was EtOAc and hexane)
11. customto give B.2

ORD record

ord-e66338672deb4ff9888f37f5761571e5

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450522B2