(Trifluoromethyl)trimethylsilane → HCID 67396746, compound

Participants

Reaction Conditions

Reaction Steps

To a 50-mL oven-dried round-bottom flask charged with tert-butyl 4-[(E)-{[(R)-tert-butylsulfinyl]imino}methyl]benzoate (0.16 g, 0.5 mmol), tetra-n-butylammoniumdifluoro-triphenylsilicate (0.30 g, 0.55 mmol), THF (8 mL) was slowly added (trifluoromethyl)trimethylsilane (0.94 mL, 0.60 mmol) in THF (2 mL) slowly at −45° C. The mixture was stirred at this temperature for 2 h, then warmed to −30° C. and stirred for 1 h. The reaction was quenched with addition of sat. NH4Cl (5 mL) and EtOAc (10 mL) at −30° C. After warming to rt, the mixture was extracted with EtOAc (2×20 mL). The combined organic phases were washed with brine (10 mL), dried (MgSO4), and concentrated. Purification via flash chromatography (10% EtOAc-hexanes to 20% EtOAc-hexanes) afforded tert-butyl 4-[(1S)-1-{[(R)-tert-butylsulfinyl]amino}-2,2,2-trifluoroethyl]benzoate (0.136 g, 72%) as a white solid. 1H NMR (Methanol-d4, 300 MHz) δ 7.98 (d, J=8.5 Hz, 2H), 7.65 (d, J=8.3 Hz, 2H), 5.15 (d, J=7.9 Hz, 1H), 1.59 (s, 9H), 1.23 (s, 9H).

Provenance & Evidence