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 T1.1 (commercially 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 for 16 hours. The reaction mixture was extracted with hexane (80×2 mL). The organic layer was then washed with saturated Na2CO3 (30 mL), brine (20 mL), and dried with MgSO4. The solvent was removed, and the residue was purified by CombiFlash® silica gel chromatography (eluent was EtOAc and hexane) to give T1.2. 1H NMR (CDCl3) δ ppm 5.56 (m, 1H), 2.36 (t, J=7.1 Hz, 2H), 1.86 (t, J=7.1 Hz, 2H), 1.16 (s, 6H).

1. customat −78° C
2. stirringstirring
3. waitwas continued at 0° C. for 2 hours
4. waitat room temperature for 16 hours
5. extractionThe reaction mixture was extracted with hexane (80×2 mL)
6. washThe organic layer was then washed with saturated Na2CO3 (30 mL), brine (20 mL)
7. dry with materialdried with MgSO4
8. customThe solvent was removed
9. customthe residue was purified by CombiFlash® silica gel chromatography (eluent was EtOAc and hexane)
10. customto give T1.2

ORD record

ord-c7606ac4fa374cea864e96f6a77ed467

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450522B2