Acetone → HCID 58382448, compound

Participants

Reaction Steps

2-Allyl-7-ethyl-6-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (0.323 g, 0.673 mmol, Preparation #14) in acetone (9 mL) and water (1 mL) was treated with NMO (0.083 g, 0.707 mmol) and 2.5 wt % OSO4 in t-BuOH (0.42 mL, 0.034 mmol). The mixture was stirred at rt for about 1.5 h. The mixture was concentrated under reduced pressure and then the material was purified using a 10 g silica column with 95:5 DCM/MeOH as an eluent to give 3-(7-ethyl-6-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)propane-1,2-diol (0.21 g, 61%): LC/MS (Table 2, Method b) Rt=2.55 min; MS m/z 514 (M+H)+.

Provenance & Evidence