Triacetoxyperiodinane → tert-butyl benzyl(4-(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine-4-carbonyl)-bicyclo[2.2.2]octan-1-yl)carbamate

Participants

Reaction Steps

To a solution of tert-butyl benzyl(4-((5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)(hydroxy)methyl)bicyclo[2.2.2]octan-1-yl)carbamate (1.26 g, 1.93 mmol) in DCM (10 mL) was added Dess-Martin periodinane (1.64 g, 3.86 mmol). The reaction was stirred at ambient temperature for about 3 h and was diluted with DCM (10 mL). The mixture was washed with saturated aqueous NaHCO3 (2×15 mL), brine (15 mL), dried over anhydrous MgSO4, filtered, and concd under reduced pressure. The resulting oil was purified by silica gel chromatography eluting with a gradient of 0-25% EtOAc in heptane to give tert-butyl benzyl(4-(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine-4-carbonyl)-bicyclo[2.2.2]octan-1-yl)carbamate (0.965 g, 77%) as a yellow oil: 1H NMR (400 MHz, CDCl3) δ 8.15 (s, 1H), 7.32-7.24 (m, 3H), 7.23-7.08 (m, 3H), 6.23 (d, J=3.5, 1H), 4.53 (s, 2H), 2.13-2.03 (m, 6H), 1.95-1.83 (m, 6H), 1.81-1.74 (m, 3H), 1.41 (s, 9H), 1.12-1.06 (m, 18H).

Provenance & Evidence