m-Chloroperbenzoic acid → 6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine

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Reaction Steps

To a mixture of 1-(2-ethyl-4-(2,2,2-trifluoroethylthio)cyclopentyl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (0.100 g, 0.200 mmol, Preparation #MMM.1) in DCM (0.667 mL) was added m-CPBA (0.090 g, 0.400 mmol). The reaction stirred at ambient temperature for about 0.5 h. The reaction mixture was quenched by the addition of saturated aqueous NaHCO3 (5 mL). The aqueous portion was extracted with DCM (2×10 mL). The combined organic layers were separated, dried over anhydrous MgSO4, filtered, and concd under reduced pressure. The crude material was purified by silica gel chromatography eluting with a gradient of 0-60% EtOAc in DCM to afford 1-2-ethyl-4-(2,2,2-trifluoroethylsulfonyl)cyclopentyl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (0.095 g, 89%, 93% purity) as a clear oil: LC/MS (Table 1, Method a) Rt=2.63 min; MS m/z: 532 (M+H)+.

Provenance & Evidence