Methyl iodide → HCID 89771086, compound

Temperature

-60 °C

To a solution of (S)-N-((R)-1-(3-chloro-5-(trifluoromethyl)phenyl)ethyl)-2-methylpropane-2-sulfinamide (1.5 g, 4.6 mmol) in anhydrous THF (20 mL) under N2 atmosphere was dropwise added LHMDS (9.2 mL, 1 M in THF, 9.2 mmol) at −60° C. The reaction was stirred for 30 min at −60° C., followed by addition of MeI (1.04 g, 6.9 mmol). The reaction was stirred at room temperature for another 3 h and quenched with water at 0° C. The resulting mixture was extracted with EtOAc (2×100 mL). The combined 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 (1.2 g, yield: 76.5%); m/z (ES+): 342 [M+H]+.

1. customat −60° C
2. stirringThe reaction was stirred at room temperature for another 3 h
3. customquenched with water at 0° C
4. extractionThe resulting mixture was extracted with EtOAc (2×100 mL)
5. dry with materialThe combined 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-4803a6fb370442fd9928efa6faa05c21

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181259B2