Acetone → HCID 58382060, compound

Participants

Reaction Steps

tert-Butyl 6-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl(2-methylallyl)carbamate (0.55 g, 0.95 mmol) and NaIO4 (0.194 mL, 3.79 mmol) were combined in a mixture of 1,4-dioxane (14.0 mL) and water (4.9 mL). To the mixture was added OsO4 (2.5 wt % in t-BuOH, 0.475 mL, 0.038 mmol) and the mixture stirred for about 6 h at rt. EtOAc (50 mL) and water (30 mL) were added and the layers separated. The aqueous layer was extracted with EtOAc (20 mL). The combined organic layers were washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (40 g Redi-Sep™ silica gel) eluting with 50-100% EtOAc/heptane. The mixture was added to NaIO4 (0.194 mL, 3.79 mmol), acetone (14.0 mL) and water (4.9 mL). To the mixture was added OsO4 (2.5 wt % in t-BuOH, 0.475 mL, 0.038 mmol) and the mixture stirred for about 3 h at rt. EtOAc (50 mL) and water (30 mL) were added and the layers separated. The organic layer was washed with brine (10 mL), dried over MgSO4, filtered, and concentrated in vacuo to give tert-butyl 6-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl(2-oxopropyl)carbamate (0.473 g, 86%): LC/MS (Table 2, Method h) Rt=2.05 min.; MS m/z: 583 (M+H)+.

Provenance & Evidence