Water → (R)-N-((S)-1-(2,3-difluorophenyl)ethyl)-2-methylpropane-2-sulfinamide

Temperature

0 °C

To a solution of (R,E)-N-(2,3-difluorobenzylidene)-2-methylpropane-2-sulfinamide (0.800 g, 3.26 mmol) in DCM (32.6 mL), cooled to 0° C. (water/icebath) under N2, was added 3M MeMgBr (4.35 mL, 13.05 mmol) in diethyl ether. Reaction mixture allowed to stir for 30 min at 0° C. Then gradually allowed to warm to room temperature and stirred for 30 min at room temperature. Reaction mixture was cooled to 0° C. then quenched with the slow addition of a saturated solution of NH4Cl and diluted with EtOAc. Phases partitioned aqueous phase extracted with EtOAc and the organic layers combined washed with water, brine, dried with MgSO4, filtered and concentrated to afford (R)—N—((S)-1-(2,3-difluorophenyl)ethyl)-2-methylpropane-2-sulfinamide (0.7868 g, 3.01 mmol, 92% yield) as yellow solid. LCMS m/z 262.0 (M+H)+, Rt 0.70 min.

1. customReaction mixture
2. temperatureto warm to room temperature
3. stirringstirred for 30 min at room temperature
4. customReaction mixture
5. temperaturewas cooled to 0° C.
6. customthen quenched with the slow addition of a saturated solution of NH4Cl
7. additiondiluted with EtOAc
8. customPhases partitioned aqueous phase
9. extractionextracted with EtOAc
10. washthe organic layers combined washed with water, brine
11. dry with materialdried with MgSO4
12. filtrationfiltered
13. concentrationconcentrated

ORD record

ord-8e914af5bebb4bb0823b02a60d6342f7

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957068B2