Methyl iodide → HCID 118492037, compound

Temperature

-60 °C

To a solution of (S)-N-((S)-1-(3-fluoro-5-(trifluoromethyl)phenyl)ethyl)-2-methyl propane-2-sulfinamide (350 mg, 1.12 mmol) in THF (10 mL) under N2 atmosphere, was dropwise added LHMDS (2.24 mL, 1 M in THF, 2.24 mmol) at −60° C. The reaction was stirred for 30 min at −60° C. followed by addition of MeI (240 mg, 1.69 mmol). The mixture was stirred at rt for another 3 h and quenched with water at 0° C. The resulting mixture was extracted with EtOAc (2×40 mL). The organic layers were dried over anhydrous Na2SO4 and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (PE/EtOAc=5/1 to 2/1) to give the title compound (270 mg, yield: 74%); m/z (ES+): 326 [M+H]+.

1. customat −60° C
2. stirringThe mixture was stirred at rt for another 3 h
3. customquenched with water at 0° C
4. extractionThe resulting mixture was extracted with EtOAc (2×40 mL)
5. dry with materialThe organic layers were dried over anhydrous Na2SO4
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel chromatography (PE/EtOAc=5/1 to 2/1)

ORD record

ord-3af5a1ca52014f63af77e576e2edc4a8

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181259B2