Methanol → HCID 66865026, compound

To a solution of ethyl 5-(3,5-difluorophenyl)-5-oxovalerate (5.00 g, 19.5 mmol) and (S)-2-methylpropane-2-sulfinamide (2.88 g, 23.8 mmol) in THF (123 mL) was added titanium tetraethoxide (8.18 mL, 39.0 mmol). The reaction vessel was quickly sealed and placed into a 60° C. bath for 16 h. After cooling to ambient temperature a septum and nitrogen inlet were attached prior to cooling to 0° C. Sodium borohydride (1.48 g, 39.0 mmol) was then added, and a complete reaction was observed after 1 h. Methyl alcohol was then slowly added until gas evolution had stopped. The reaction mixture was then diluted with brine (60 mL) while experiencing rapid stirring. The resultant slurry was filtered through celite, washing with EtOAc as needed. The combined organics were then washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give an oil. This oil was purified by silica gel chromatography, eluting with a gradient of EtOAc:Hexanes—10:90 to 50:50, to give the title compound. MS: m/z=362 (M+1).

1. customThe reaction vessel was quickly sealed
2. customplaced into a 60° C.
3. customfor 16 h
4. temperatureto cooling to 0° C
5. customa complete reaction
6. filtrationThe resultant slurry was filtered through celite
7. washwashing with EtOAc
8. washThe combined organics were then washed with brine
9. dry with materialdried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customto give an oil
13. customThis oil was purified by silica gel chromatography
14. washeluting with a gradient of EtOAc

ORD record

ord-c574c4ebe1f240df90021e9ef5985fc5

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07893079B2