tert-Butylsulfinamide, (S)-(-)- → (NE,S)-2-methyl-N-[2,2,2-trifluoro-1-[4-(6,6,6-trifluorohexoxy)phenyl]ethylidene]propane-2-sulfinamide

To a solution of Intermediate 8B (717 mg, 2.184 mmol) and (S)-2-methylpropane-2-sulfinamide (529 mg, 4.37 mmol) in THF (10 mL) was added tetraethoxytitanium (1993 mg, 8.74 mmol) in THF (20 mL). The resulting mixture was reflux for 5 h. TLC (20% EtOAc in hexane) indicated the starting ketone was completely consumed. The solvent was evaporated to afford a yellow oil. This yellow oil was dissolved in EtOAc and then washed with saturated NaHCO3 (25 mL) and a large amount of white precipitation formed which was removed by filtering through a bed of Celite®. The white precipitation was rinsed with EtOAc. The combined EtOAc solution was washed again with saturated NaHCO3, dried (MgSO4) and concentrated. The crude product was purified by silica gel chromatography (40 g silica gel, eluted with EtOAc in hexanes) to afford Intermediate 8C (620 mg, 66%).

1. temperatureThe resulting mixture was reflux for 5 h
2. customwas completely consumed
3. customThe solvent was evaporated
4. customto afford a yellow oil
5. washwashed with saturated NaHCO3 (25 mL)
6. customa large amount of white precipitation
7. customformed which
8. customwas removed
9. filtrationby filtering through a bed of Celite®
10. customThe white precipitation
11. washwas rinsed with EtOAc
12. washThe combined EtOAc solution was washed again with saturated NaHCO3
13. dry with materialdried (MgSO4)
14. concentrationconcentrated
15. customThe crude product was purified by silica gel chromatography (40 g silica gel, eluted with EtOAc in hexanes)

ORD record

ord-8c3c0caf30f04112a83ad239e4f9cce8

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08791091B2