Ammonium Chloride → N-[(1R)-1-cyclopropyl-2,2,2-trifluoroethyl]-2-methylpropane-2-sulfinamide

Temperature

-55 °C

N-[(1E)-Cyclopropylmethylene]-2-methylpropane-2-sulfinamide ((S), 10.0 g, 57.7 mmol) and TMAF (6.45 g, 69.3 mmol) were placed in a flask and dissolved in THF (290 mL). The flask was purged with N2. The solution was cooled to −55° C. and a solution of TMSCF3 (13.53 ml, 87 mmol in 430 mL of THF) was added via syringe slowly. The mixture was stirred at −55° C. until the reaction was complete. The solution was warmed to −10° C. and treated with sat. NH4Cl (10 mL). The mixture was extracted with EtOAc, and the combined organics were dried, and concentrated. The diastereomers were separated by flash chromatography to give the title compound. 1H NMR (600 MHz, CDCl3) δ 3.32 (d, 1H); 2.93 (m, 1H); 1.24 (s, 9H); 1.08 (m, 1H); 0.82 (m, 1H); 0.72 (m, 1H); 0.67 (m, 1H); 0.52 (m, 2H).

1. customThe flask was purged with N2
2. temperatureThe solution was warmed to −10° C.
3. extractionThe mixture was extracted with EtOAc
4. customthe combined organics were dried
5. concentrationconcentrated
6. customThe diastereomers were separated by flash chromatography

ORD record

ord-4d43e7b1525c4d41ad4e4d7c4da3a326

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08431569B2